0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via Method 1: Synthesis of Quaternary Ammonium Compounds from Primary and ­Secondary Amines

DOI: 10.1055/sos-SD-040-00546

Kruiswijk, E.; Deck, J. A.Science of Synthesis, (200940817.

Primary and secondary amines can be alkylated with alkyl halides or similar compounds in the presence of a base to afford the corresponding quaternary ammonium salts 1 or 2 (Scheme 1).[‌1‌,‌2‌] These alkylations work best when the base (B), normally an alkali metal hydroxide or an alkali or alkaline earth metal salt, is more basic than the amine, so that further reaction with the alkylating reagent (always used in excess) is suppressed. Furthermore, the quaternary ammonium salt is much easier to isolate and purify if the salt (BHX) formed as a byproduct has orthogonal solubility.

Meeeee 8 Meeeeeeeee ee Meeeeee eee Meeeeeeee Meeeee[‌8‌,‌8‌]

M eeeeeee ee eeeeeeeeee eeeeeeee eeeee eee ee eeeeee ee eee-eeee eeeeeeeee eeeeeee ee eeeeeeee eeee eee eeeeee eeeeeeee ee eeeeeee eeeeeeeee eeee eeeeeeeee ee eee eeeee eeeeee 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeee ([eeee][Me])[‌8‌] (Meeeee 8).[‌8‌] Mee eeeeee ee eee eeeeeeeeee eeeeeeee eeeee eeeeeeee eeeeee eeee eee eeeeee ee eee eeeeeee eeeeeeee eeee eee eee eeeee eeeee ee eee eeeeeee eeeeeeeee eee, ee eeeeeeee, eeee eeeeeeee eeeeeeeee ee eeeeeee eeee eeeeeeee eeeee eeeeeee eeeeeeeee eeeeee eee eeeeee ee eee eeeeeeeeee eeeeeeee eeeee eeeeeeee eeeeeeee ee eee eeeee Me MM8 Me > M > MM88 > M8M88 MM88 MMe. Me ee eeee eeeeeee eeee eeeeeeeee eeeeeee eeeeeee eeeeeeeee eee eeeeeeee eeeeeeee, eeeeeee, ee eeeeeeeee eeeeee eeee eeeeeeeeee ee eeee eeeeeeeee eeee eeeeee.

Meeeee 8 Meeeeeeee ee Meeeeeeeee Meeeeeee Meeee eeee Meeee Meeeeeee Meeee Meeee 8-Meeee-8-eeeeeeeeeeeeeeeee Meeeeee ee e Meeeeeee[‌8‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeeeeeeee Meeeeee 8 (M8=Me; M=M); Meeeeee Meeeeeeee:[‌8‌]

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.

M eeeeeee ee e eeeeeee eeeee (8.8eee), MeMMM8 (88.8e, 8.8eee), MeM (88.8e, 8.8eee), eee MeMM eee eeeeeeee eee 88e [eeeee 88e eee 88e, eeee MeM (eeeee 88.8e, 8.88eee) eee eeeee]. Mee eeeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee eeee MMMe8 (8 ×). Mee eeeeeeee eeeeeeee eeee eeeeeeee eee eee eeeeeee eee eeeeeee eeee eee eeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee e eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee.