N- 2-Bromoallyl ethylamine

N-(2-Bromoallyl)-ethylamine with sodium amide in liquid ammonia gave N-ethylallenimine (154) by either of the paths shown (116,117). 

The reported boiling point of N-(2-bromoallyl)ethylamine is 148-153°. It is strongly recommended that the product and other 2-haloallylamines be distilled at reduced pressure under nitrogen, for the submitters have noted two instances when a 2-haloallylamine polymerized with considerable evolution of heat during slow distillation at atmospheric pressure. 

This method is essentially that described by Pollard and Par-cell.8 No other procedure appears to have been used to prepare N-(2-bromoallyl)ethylamine. A number of N-(2-haIoaIIyl)alkyl-amines have been prepared by treatment of a 2,3-dihalopropene with a primary alkylamine in water,8-4 ether,8-4 or benzene.5... 

The method described is essentially that of Pollard and Par-cell.4 N-Ethylallenimine has been prepared by treating N-(2-bromoallyl)ethylamine in liquid ammonia with sodium amide,4-6 lithium amide,6 or potassium amide.6... 

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