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Reaction of N ‐benzyl‐1,1′‐iminobis‐2‐butanols with 70% w/w sulfuric acid
Author(s) -
Hernestam Sven,
Stenvall Gillis,
Olsson Thomas
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210304
Subject(s) - chemistry , sulfuric acid , amine gas treating , medicinal chemistry , n butanol , benzyl alcohol , butanol , organic chemistry , ethanol , catalysis
Treatment of ( S:R )‐ N ‐benzyl‐1,1′‐iminobis‐2‐butanol with 70% w/w sulfuric acid gives cis ‐ and trans‐N ‐benzyl‐2,6‐diethylmorpholines (15 and 74%, respectively) and N ‐alkenyl‐4‐ethyl‐1,2,3,4‐tetrahydroisoquinolines (5%). Hydrogenation of the reaction mixture gives cis ‐ and trans ‐2,6‐diethylmorpholines and N ‐butyl‐4‐ethyl‐1,2,3,4‐tetrahydroisoquinoline. Neither N ‐benzyl‐ N ‐crotyl‐(2‐hydroxy‐1‐butyl)amine ( 4 ) nor N ‐benzyldicrotylamine ( 5 ) are intermediates in the reaction. ( S:S )‐ N ‐Benzyl‐1,1′‐iminobis‐2‐butanol gives 95% of cis‐N ‐benzyl‐2,6‐diethylmorpholine and 1% of the trans isomer.