Formaldehyde → HCID 22406718, compound

Participants

Reaction Steps

Sodium cyanoborohydride (2.8 g) was added at 5° C. to a mixture of 1-[1-(2,4-dichlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (10 g, prepared as described in Example RC4), methanol (100 ml) and 37-40% aqueous formaldehyde solution (7.2 ml). The mixture was warmed to ambient temperature and stirred for 1.5 hours. The solvent was removed in vacuo and the residue partitioned between water and dichloromethane. The organic phase was washed with concentrated ammonia solution, then water, and dried over magnesium sulphate. The solvent was removed in vacuo to yield 1-[1-(2,4-dichlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline as a gum which solidified on standing.

Provenance & Evidence