Ch18 Amines(pdf) - KFUPM Open Courseware

Synthesis of Amines via AmidesOCOHonly LiAlH 4 is anappropriate reducingagent for this reaction1. SOCl 22. (CH 3 ) 2 NH(86-89%)89%)1. LiAlH 42. H 2 OOCN(CH3 ) 2Reductive AminationCH 2 N(CH3 ) 2(88%)Synthesis of Amines via Reductive AminationIn reductive amination, , an aldehyde or ketoneis subjected to catalytic hydrogenation in thepresence of ammonia or an amine.Synthesis of Amines via Reductive AminationThe imine undergoes hydrogenation fasterthan the aldehyde or ketone. . An amine isthe product.RfastRRfastRCO+ NH 3CNH + H 2 OCO+ NH 3CNH + H 2 OR'R'The aldehyde or ketone equilibrates with theimine faster than hydrogenation occurs.R'R'RCHNH 2R'H 2 , Ni