Conversion of benzyl alcohols into benzyldimethylamines by hexamethylphosphoric triamide

Abstract

Suinvzary Benzyl alcohols react readily with hexamethyl-The chemistry of HMPT,4*5 as well as thc report by White phosphoric triamide (HMPT) a t reflux affording the and Elligerg on the reactions of the analogous NN-dimethylcorresponding benzyldimethylamines in modest yield.sulphamates, suggest the reaction pathway ( 1) and (2).

Acid catalyzed pressure synthesis of N,N‐dimethylbenzylamine from benzylamine and methanol

“…The standard free energy change (AGO) at 298 K for reaction (1) has been calculated by using the relationship AG"=AH"-TAS" (2) where AH' and AS" are, respectively, the standard enthalpy change and standard entropy change of the reaction. The standard free energy change (AGO) at 298 K for reaction (1) has been calculated by using the relationship AG"=AH"-TAS" (2) where AH' and AS" are, respectively, the standard enthalpy change and standard entropy change of the reaction.…”

“…should increase with pressure. The standard free energy change (AGO) at 298 K for reaction (1) has been calculated by using the relationship AG"=AH"-TAS" (2) where AH' and AS" are, respectively, the standard enthalpy change and standard entropy change of the reaction. The standard heats of formation and entropies for methanol and water at 298 K are available from the literature', but those of benzylamine and DMBA, being unavailable, have been calculated by the group contribution method developed by Benson and colleagues.…”

“…Thermodynamics of Reaction(1) wherefis the fugacity of the gas and y is the fugacity coefficient of the gas.…”

Reaction of benzoins with hexamethylphosphoric triamide. Convenient synthesis of 2,3,5,6-tetraarylpyridines

“…Received February11, 1975 In the course of our investigation2 on the reaction between hexamethylphosphoric triamide (HMPT) and benzyl alcohols to give IV,N-dimethylbenzylamines, we treated benzoin (la) with HMPT in an attempt to prepare the corresponding cr-dimethylaminodeoxybenzoin(2). After a 30min reflux, the solution was subjected to a water work-up and an 18%yield of 2,3,5,6-tetraphenylpyridine (3a) was isolated (Scheme I).…”