Science of Synthesis

Lawrence, S. A., Science of Synthesis, (2009) 40, 526.

The alkylation of primary, secondary, and tertiary amines with alkyl halides is simpler and more controllable than the corresponding reaction with ammonia. Treatment of primary amines with alkyl halides yields a mixture of secondary and tertiary amines, and quaternary ammonium salts, depending upon the reaction conditions. The reaction between tert-butylamine and iodomethane in a 2:1 ratio in xylene gives a mixture of tert-butyltrimethylammonium iodide (34%), tert-butyldimethylammonium iodide (20%) and tert-butylmethylamine (7%).[‌114‌]

Mee eeeeeeeee ee eeeeeeeee eeeeee ee eee eeeeeeee ee eeeee eeeeeee eeee eeeeeee eeeeee eee eeee eeeeeeee.[‌888‌] Meeee eeeeeee eeee eeeeeee eeeeeeeee eeeeeeeeee ee eeeeeeeeee eeeeee eee eee eeee eeee eeeeeeeeeeeee. Meeee eeeeeeee eee ee eeeee eeeeeeeeee eee eeeee eeeeeee eeeeeeee eeeeeeeeeeee, eeeeeeee eeeeeee eeeeeeee (eee eeeeeeeee) eee ee eeee ee eee eeeeeeeeeee eee eeeeeeee. Meee eeeeeee ee eeeeeeeeee eeeeeeeee ee eeeeeee eeeeee ee eeee eeeeeeee ee eeeeeeeee eeeeee ‌88‌ eee eeeeeeee eeeeee ‌88‌ eee eeeee ee ‌Meeeee 88‌.

‌Meeeee 88‌ Meeeeeeeee ee Meeeeee Meeeee eeee Meeee Meeeeee[‌888‌,‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

e Meeee eee eeeeeeee.

Me e eeeeeeeee eeeee ee eeeeeeee eee eee eeeeeeeee ee e eeeeeeee eeeee ee ee ee eeeeeee, eee eeeeeeeeeee eeeeeeeee eeeeee eee eeee ee eee e eeeee eeeeee ee eee eeeeeee eeeee eeeeeeee ee eee eeeee eeeeee eee ee eeeeeeeee eeee eeee ee eeeeeeeee eeeeeeeee ee ee eeeeeee eeeeeee eeee ee eeeeeeee eeeeeeeee ee eeeeeeeeeeee. Meeeeee, eeee eeeeee ee eeee eeeeeeee eee eeeeeeeee ee eee eeeeeeee eeeee ee eeeeeeeee ee eeeeeeeeee ee ee ee e eeeeeee eeeeeee eeee ee eeee ee eeeeeee, eeeeee eeeee ee eeeeeee eeeeeee ee eee eeeeeeee eeeeeeeeee.[‌888‌]

Meeeee eeeeeeeee ee eeee ee eee eeee ee eee eeeeeee-eeee eeeeeeeeee ee e eeeee ee eeeeee eeeee 8-eeeeeeeeeeeee-8,8-eeee eee ee eeee ee eeeeeeeeeee eeee eeeeeeeee eeeeee ee eeeeeeee eeeeeeeeeeee ee 888–888°M (‌Meeeee 88‌).[‌888‌] Mee eeeeeee eeeeee eee eee eeeeeeee ee eee eeeeee eeeeeeee, eeeee eeeeee eee eeeeeeeeeee ee eeeeeee eeeeeeeeee eeeeeeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeeee ee Meeeeee Meeeee eeee e Meeeee Meee[‌888‌]

Mee eeeeeeeeee eeeeeeee ee eeeeeeee eeeeeeeee ee eee eeeee eeeee eeeeee. Mee eeeeeee, eeeeeeeeeeeeeee eeeeee eeeeeee eeee eeeee eeeeeeee ee eeeeeeee eeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee ee 88°M. Mee eee ee 8-eeeeeeeeeee eeeeeee ee eeeeeeeeeeee eeeeee eeee eeeeee (88%) ee eee eeeeeeee eeeee eeeeeee(eeeeeeeeee)eeeee. Me 8-eeeeeeeeeee ee eeee, eeeeeeeeeeeeee eeeeee, eeeeee eeeeeeeeee(eeeee)eeeee ee 88% eeeee.[‌888‌] Me M-eeeeeeeeeeeeeee ee eeeeeeee, e eeeeee eeeeeeeee eeeeee eeeee ee ee eee eee Meeeeeeeee–Meeeee eeeeeeeeeeee ee eee Meeeeeee eeeeeeee eeee eeeeee eeee eee eeeeeeeeeeee.[‌888‌]

Meeeeeeeeee eee ee eeeeeeeeeeeee eeee e eeeeee eeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeee eeeeee ee eeeeeeeeeeeeeee ee eeee e eeeeee eeeeeeeee eeeee ee eeee eeeee.[‌888‌] Meee eeeeeeeeeeee eeeeeeee eee eeee eeeeeee ee eee eeeeeeeeeee ee e eeeeee ee M-eeeeeeeee eeeeeeeee eeeeee α-eeeee eeeeee eeee eeeeeee α-eeee eeeeeeeeeeee eeeeee.[‌888‌]

Me eeeeeee, eee eeeeeeeeee ee eeeeeeeeee eee eeeeeeee eeeeee eee eeee eeeee ee ee eeeeeeeeeee ee eee eee ee 8,8-eeeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeee-8(8M)-eee (MMMM) ee e eeeeeee. Mee eeeeeee, eeeeeeeee ee (M)-8-eeeeeeeeeeeeeeee ee 8,8-eeeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeee-8(8M)-eee eeee 8 eeeeeeeeeee ee eeeeee eeeeeeeee eeeeeeee ee eee eeee eeeeeeee ee eeeeeee eeeee (M)-M-eeeee-8-eeeeeeeeeeeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeee ee e Meeeee Meeee ee 8,8-Meeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeee-8(8M)-eee[‌888‌]

8,8,8-Meeeeeeeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeee eeee eeeeeee eeee eeeeee ee 88–88°M: eeeeeee ee eeeeeee ee eeeee eeeeee, ee eeeee eeeeeeee eeeeeeee ee eeee 8,8-eeeeeeeeeeeeee eee eeeeeeee eeeeeeee.[‌888‌] Me eeeee eeeee ee eeee, eeeee eeeeeeee eeeee eeeeeeeeee eeeeeeeeeeeeeeeeeee eee eeeeeee eeee M-eeeeeeeeee eeeeeeeee, eeeeeeeeeeee eeee eeeee eeeeeee eeeeeeeeeeeee (ee eeeeeeeee eeeeeeeee) ee eeee eee eee eeeeeeeee eeeeeeeeee ee eeeeeee eeeeee eeee eeeeeeee eeeee eeeeeee.[‌888‌] M eeeeeeee ee eeee eeeeeee eee eeee eeeeeeee ee eeeeeeeee eeeeeee eeeeee ee eeeeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeee (‌Meeeee 88‌).[‌888‌] Mee eeeeee eeee ee eeeeeeeee ee eeeeeeeeeee eeeeeeeee eeeeeeeeeeeeee eeeeeeeee. Meee eeeeee eee eeee ee eeee eee eee eeeeeeeeee ee eeeeeeee eee eeeeeeeeee eeee 8-eeeeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeeeee eeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeee ee 8-Meeeeeeeeeeeeeee eeee 8-Meeeeeeeeee[‌888‌]

Mee eee ee eeeeee eeeeeeeee eee eeee eeeeeeee ee eee eeeeeeeee eeeeeee eeeeeee eeeeee ‌88‌ eee eeeeeeeeeee eeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeeee ee Meeeeee Meeeee eeee Meeeeeeeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeee ee eeeeeeeee eeeeee eeee eeeee eeeeeee ee e eeeeee eeee eeeeeeeee ee eeeeeee eeeeeeee eeeeee ‌88‌ ee eeeeeeeeee eeee eeeeeeeee ee eeeeeee eee.[‌888‌] Meeeeeeee eeeee eeeeee eee ee eeeeeeeeee eeee e eeeeeeeee eeeee eee eeeee eee eeeeeeeee eeeee ee e eeeeee eee eeeeeeee eee ee eee eeeeeee e eeeeeee.[‌888‌] Meee eeeeeee eeeeeeee ee eee eeeeeeeee ee eeeeeeeee eeeeee eeee eeeee eeeeeee eee eeeee ee ‌Meeeee 88‌.

‌Meeeee 88‌ Meeeeeeeee ee Meeeeeeee Meeeee[‌888‌,‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeeeeeeeeeeeeee eee ee eeeeeeeee eeeee eeeee eeeeeee eee eeeeeeeeee ee eee eeeee ee e eeeeeeeeee Meeeeeeeee eeeee, eeeeeeeeeeeeee, eee eeeeeeee. Me eeeeeee ee eeeeeeeeeee ee ‌Meeeee 88‌.[‌888‌]

‌Meeeee 88‌ Meeee-Meeee Meeeeeeeee ee e Meeeeeeeeeeeeeeeeeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeee eeeeeee eeeeeee eeee eeeeeeeeeeeee eeeee eeeeee eeee eeeeeee eeeeeeeee ee eeee ee eeeeee ee eee eeeeeeee eeeeeeee eeeee. Mee eeeeeee, eeee eeeeeeee eeee eeeeeeeeeeee, eeee 8-eeeeeeeee-8-eee (‌88‌) eee 8-eeeeeeeee-8-eee (‌88‌) eeee M,M-eeeeeeeeee-8-ee-8-eeeee (‌88‌) (‌Meeeee 88‌).[‌888‌] Me ee eeeee eeeeee eeee eeeee eeeeeeeee eeee eeee eeeeee eeeee eeeeeee-eeee eeeeeeeeee, eee eeee eeeeeee ee eeee ee eeeeeee, eee eeeeee eeee eeeeeeeeeeee.

‌Meeeee 88‌ Meeeeeee ee Meeeeee Meeeeeeee eeee Meeeeeeee Meeeee[‌888‌]

Me eee eeeeeeee ee e eeeee eeeeee(8)/eeeeee(M) eeeeeeeee eeeeee (eee eeee ‌Meeeee 88‌), eeeeeeee eeeeeeeee eeeeeee eeeeeeee eeeeeeeee eeeeee, ee eeee eeeeeeeee eeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeee. Mee eeeeeee, eeeeeeeeee eeeeee eeee 8-eeeeee-8-eeeeeeeee-8-eee ee eeee eee eeeeeeeeeee eeeee ‌88‌ ee eeee eeeee ee eee eeeeeeee ee eee eeeeee eeeeeeee, eeeeeee eee eeeeeeeeeee eeeeeeee eeeee eeee eeeeee eeee eeeee eeeeeeee eeeeeeee eeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeee-Meeeeeeee Meeeeeeee ee e Meeeeeeeeee Meeee[‌888‌]

Mee eeeeeeeee-eeeeeeeee eeeeeeee ee eeeeeee eeeeeeeee eeee eeeeeeeee eeeeee eeeee eeeeeee eeeeeeee eeeeee (‌Meeeee 88‌). Mee eeeeeeee eee eeee ee eeeeeee eee eeeeeee eeeeeeeee, eee eeeeee eeeeeeeeeeee eee eeeeeeee. Meee eeeeeeeeeee eee ee eeeeeee ee eeeeee eeeeeeeeeeeee, eee ee eee eeeeeeeee ee eeeeeeeee eeeeee eeee eeeeeee eeeeee.[‌888‌] Mee eeeeeee eeeeeeee ee eee eeeeeeeee-eeeeeeeee eeeeeeeee ee eeeeeee eeeeee eee Meeeeee ‌88.8.8.8.8.8‌

‌Meeeee 88‌ Meeeeeeee ee Meeeeee Meeeee eeee Meeeeee Meeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

e Mee eeeeeeee ee eeeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee.

e Mee eeeeeeee ee eeeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee.

Meeeeee eeeeeeeeeeeee eee eeee eeeeeeee ee ee ee eeeeeeeee eeeee eee eee eeeeeeee eeeeeee eeeeeeeeeeeee eee eeeeeee eeeee eeeeeeee ee eeeeeeeeeeeeeee ee eeee eeeeeeeeeeeeeeeeeee eeee eeee ee eeeeeeeee eeeeee.[‌888‌] Meeeeeeee eeeeee (eeeeeeeeeeee, eeeeeeeeee, eee eeeeeeeeeee) eeeee eeee eeeeeeeeeeeeee ee eee eeeeeeee ee eeeeee eeeeeee ee eeeeeeeeeeeee/eeeeeeeeeeeeeeeee ee eeee eee eeeeeeee eeeeee ee eeeeeeee ee eeee eeeeee.[‌888‌] Me eeeeeeeee eeeeeee eeeeeeeee ee eeeeeeee eeeeee ‌88‌ ee eeeeee eeeeeeeeee ee eeeeeeeee eeeeee ‌88‌ eeee eeeee eeeeeee ee M,M-eeeeeeeeeeeeeeeeeeeee (Müeee'e eeee) eee eeee eeeeeeee (‌Meeeee 88‌). Mee eeeeeeeee ee eeeeeeeeee eeeee eee eee eee ee eeeeeeeeee eeeeeeeee ee ­eeeeeee.[‌888‌] Mee eeee ee M,M-eeeeeeeeeeeeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeee ee eee eee-eeeeeeeeeeee eeeeeeeee, eeeeeeee ee ee eeeeeeeee ee e eeee eeee eee eeeeeeee eeeeeee eeeeeeee ee eee eeeeeeee.

‌Meeeee 88‌ Meeeeeeeee ee Meeeeeeee Meeeee eeee Meeee Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeee eeee eee eeeeeeee eeeee eee eee eeeeeeeee eeeee eee ee eeeeeee eeee (eeeeeeeeeeee)eeeeee ee eee eeeeeeee ee eeeeee eeeee ee eeeeee eeeeeeeee ee eeee eee eeeeeeeee eeeeee ee eeeeeeeee eeee eeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meee-Meeeeeee Meeeeeeeee ee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

M,M-Meeeeeeeee-8-ee-8-eeeee (‌88‌, M8 = MMMeMM=MM8; M8 = Me):[‌888‌]

MeM (888 e, 888 eeee) eee eeeee eeeeee ee eee-8-ee-8-eeeee (88 e, 888 eeee) ee e eeeee eeeeee eeee e eeeeee eeeeeeeee eee eeeeee ee ee eee eeee. Mee eeeeeeee eee eeeeeeeeee eee eee eee eeee eee eeee ee eeee eee eeeeeeeeeee ee eee eeeeeee eeeee eeeeee. Meeee eee eeeeeeee eee eeeeeeee, eeeeeeee 88% MMM (88.8 e, 888 eeee) eee eeeee eeeeee ee eee eeee ee eeeee eeeeeeee eeee eeeeeee ee eeeeeeee e eeeeee eeeeee. Meeee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeee ee e eeeee eeee eee 8 e eeeee eeeee ee eeeee eeeeee ee M8M eee eeeee eee eee eeeeeeeee eeee eee eeeeeeeeeeee ee eeeeeee. Mee eeee eeeee eee eeee eeeeeeeee ee eeeeeeee ee ee MMM eee eee eeeee eeeeeeee eeee eeee eeeeeeeee ee eeeeeee eeeee M,M-eeeeeeeeee-8-ee-8-eeeee, eeeee eee eeee eeeeeeeeeee; eeeee: 88 e (88%).

Meeee(eeeeee)(eeeeee)eeeee [‌88‌, M8 = Me; M8 = Me; M8 = (MM8)8Me]:[‌888‌]

Meeee Me(MM8)8Me (88.8 e, 8.8 eee) eee eeeeeeeee ee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee) eee eee eeee eee eeeeee ee ee eee eeee. MeMMMe (88 e, 8.88 eee) eee eeee eeeee eee eee eeeeeee eee eeeeeee ee eeeee ee ee eee 88 e. Me8M (888 eM) eee eeeee eee eee eeeeeeeee eeee eee eeeeeeeee eeee 88% MMe (8 × 888 eM). Mee eeee eeee eeee eee eeeeee eee eeee eeeeeeee eeeeeeee eeee MeMM. Mee eeeeeeeee eeeee eeeeeee eeee eee eeee eeeeeeeee eeee Me8M (8 × 888 eM) eee eee eeeeeeee eeeeeeee eeee eeeeeeee, eeeee eeeeeeeee (MMM eeeeeee), eeeeeeeeeeee, eee eeeeeeee ee eeeeeeeeeeee; eeeee: 88.8 e (88%); ee 88–88°M/8 Meee.

Meeeeeee Meeeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeeeee eeeee ‌88‌ (8.8 e, 8 eeeee), eMe8MMe (8.8 eeeee), eee eeeee eeeeeee (8.8 eeeee), eee MeMM (88 eM) eeee eeeeee ee e eeeee eeeeeeee eeeee eee eeeeeee ee ee eeeee M8. Meeee eeeeeeeeee (eeeeeeeee ee MMM), eee eeee eee eeeeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee MM8Me8 (8 eM) eee eeeeee eeee eeeeeeeee M8M (8 eM). Meee eeeeee eeee eeeeeeee eee eee eeeeeee eeeee eee eeee eeeeee eeee MM8Me8 (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeeeeee eeee eeee eeeee (MeMM8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 88.
• 8.Meeeee-Meee, (8888) 88/8, 88.
• 8.Meeeee-Meee, (8888) 88/8, 88.
• 8.Meeeee-Meee, (8888) M 88e8, 888.