Science of Synthesis

Wille, U., Science of Synthesis, (2009) 40, 918.

N-Chloropyrrolidines ‌70‌ (n = 1) and piperidines ‌70‌ (n = 2) can be synthesized from the parent heterocycles, or their hydrochlorides, by treating them with N-chlorosuccinimide using either a vacuum gas/solid chlorination technique,[‌24‌,‌133‌] or as solutions in tetrahydrofuran,[‌204‌] diethyl ether[‌89‌,‌134‌,‌200‌] or dichloromethane.[‌201‌,‌205‌] Enantiomerically pure (R)-(–)-1-chloro-2-methylpyrrolidine (‌71‌) is obtained from (R)-2-methylpyrrolidine using N-chlorosuccinimide in diethyl ether.[‌193‌] Similar conditions can be applied to the N-chlorination of 2,3-dihydro-1H-benzo[de]isoquinoline (‌72‌) (‌Scheme 42‌).[‌206‌]

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(M)-(–)-8-Meeeee-8-eeeeeeeeeeeeeeeee (‌88‌):[‌888‌]

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M eeee ee (M)-(–)-8-eeeeeeeeeeeeeeeee (8.88 e, 8.88 eeee) ee eee Me8M (8 eM) eee eeeeee eeeee eeee eeeeeeee ee e eeeeeeeeee ee MMM (8.8 e, 88.8 eeee) ee eee Me8M (88 eM), eee eee eeeeeee eee eeeeeee eee 8 e. Mee eeeeeeeeeee eee eeeeeeee eee eee eee eeeeeee eee eeeeeee. Meeeeeeeeeee (eeee eeeeeeeeeee ee ee 88°M) ee eee eeeeeee eeee eee eeeee eeeeeeee; eeeee: 8.88 e (88%); ee 88–88°M/88 Meee; [α]M88 −88.8 (e 8.88, MeMM).

References

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• 8.Meeeee-Meee, (8888) M 88e8, 888.