Oxalic Acid → (2-Benzyl-1,2,3,4-tetrahydroisoquinolin-1-YL)methanamine

Participants

Reaction Steps

Title Compound I, in which R=CH2C6H5 ; R'=H; A=CH; pY=C2H2O4, q=0 and n=1, was prepared by reducing 2-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide (6.7 g; 0.025 mole) with LiAlH4 by the same procedure as used in Example I to obtain 3.77 g (60% theory) of 1-aminomethyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline as a yellow oil. This compound was reacted with benzaldehyde and reduced as in Example II. The resultant 1-(N-benzyl)aminomethyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline was propionylated as in Example I and the oxalate (having a melting range of 159°-61°) formed.

Provenance & Evidence