2-Chlorobenzaldehyde → 1-(2-Chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

To a mixture of 2-chlorobenzaldehyde (0.5 M in dichloromethane) (800 μl) and 2-(3,4-dimethoxy-phenyl)-ethylamine (0.25 M in dichloromethane) (800 μl) was added trifluoroacetic acid (150 μl). The mixture was shaken at room temperature for 12-24 hours then evaporated to dryness. Toluene (1 ml) was added the mixture vortexed and re-evaporated to dryness. The residue was dissolved in methanol (1.5 ml) and dichloromethane (1 ml) and filtered through a SCX cartridge (Bakerbond JT7090-07, aromatic sulfonic acid). The cartridge was washed with methanol (3 ml) the product eluted with 0.5 M ammonia solution (5 ml). Product containing fractions were combined and evaporated to dryness. Toluene (1 ml) was added the mixture vortexed and re-evaporated to dryness to give 1-(2-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline which was used directly in the next step.

Provenance & Evidence