Formaldehyde → HCID 13027030, compound

Participants

Reaction Steps

A reaction mixture of 0.96 g (0.003 m) of N-(2-chlorobenzyl)-1-(3,4-dimethoxyphenyl)-2-aminoethanol from Example 5, 3 ml (0.037 m) of formaldehyde and 0.4 g of sodium borohydride in methanol was reacted to give 0.94 g (93%) of N-(2-chlorobenzyl)-1-(3,4-dimethoxyphenyl)-2-methylaminoethanol as an oil. This material (0.6 g., 0.0018 m) and 0.95 g (0.007 m) of aluminum chloride were reacted as described to give 0.42 g (66%) of 8-chloro-4-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride, m.p. 212°-217°. This material (0.68 g., 0.002 m) and 1.2 ml (0.013 m) of boron tribromide were reacted to give 0.70 g. (94%) of 8-chloro-4-(3,4-dihydroxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide, m.p. 266°-269°.

Provenance & Evidence