A new strategy for the preparation of secondary amines via o- (tetrahydropyranyloxymethyl)-benzamides

Article abstract of DOI:10.1016/S0040-4039(98)00990-3

The new synthesis strategy for the preparation of secondary amines starts from N-alkyl-phthalimides which are reduced to the corresponding o- hydroxymethyl-N-alkyl-benzamides. After protection of the hydroxy group as tetrahydropyranyl ether the N-alkyl-benzamides are alkylated to o- (tetrahydropyranyloxymethyl)-N,N-dialkyl-benzamides. The deprotection of the hydroxy group and the release of the secondary amines can be achieved in execellent yields in one reaction step using aqueous acetic acid.