Ethylamine → HCID 20283269, compound

Participants

Reaction Steps

To a stirred solution of ethylamine (100 ml) in methanol (250 ml) maintained under nitrogen and cooled in an ice bath was added portionwise 1-chloromethyl-3,4-dihydro-4-phenylisoquinoline (10.0 g, 0.033 m) and the mixture heated to 50°-52° C. for 2 hours. After cooling, the solution was poured into a pressure bottle and hydrogenated on a Parr apparatus over 10% Pd/C catalyst (2.0 g) at 40 psi for 1 hour. The catalyst was removed by filtration and the solvent evaporated to a gummy residue. This residue was dissolved in methanol (50 ml) and isopropanol (50 ml) and acidified with HCl gas. Upon cooling and standing, a white solid crystallized which was collected by filtration. Recrystallization from methanol/isopropanol/water and vacuum drying gave 7.6 g of the major isomer of 1,2,3,4-tetrahydro-1-(ethylamino)methyl-4-phenylisoquinoline dihydrochloride, m.p. 241°-242°.

Provenance & Evidence