Dimethylamine → HCID 20283262, compound

Participants

Reaction Steps

To a stirred solution of dimethylamine (250 ml) in methanol (1 liter) maintained under nitrogen and cooled in an ice bath was added portionwise 1-chloromethyl-3,4-dihydro-4-phenylisoquinoline (25.0 g, 0.084 m) and the mixture stirred for 4 hours while being allowed to warm to ambient temperature. The solution was poured into a pressure bottle and hydrogenated on a Parr apparatus over 5% Pd/C catalyst (5.0 g) at 40 psi. for 16 hours. The catalyst was removed by filtration and the solvent evaporated to a gummy residue. The residue was dissolved in methanol (300 ml) and isopropanol (100 ml) and acidified with HCl gas. Upon cooling and standing, a solid crystallized which was collected by filtration. Recrystallization from methanol/isopropanol/water gave 12.2 g of the major isomer of 1,2,3,4-tetrahydro-1-dimethylaminomethyl-4-phenylisoquinoline dihydrochloride as a monohydrate, m.p. 278°-279°.

Provenance & Evidence