GS 389 → 4,4-Diphenylheptane

Participants

Reaction Steps

The 1,2,3,4-tetrahydro-1-(4-methoxybenzyl)-6,7-dimethoxyisoquinoline was reacted with 7-[N-3-(4-fluorophenyl)propionyl]amino-4,4-diphenylheptanal in the presence of sodium cyanoborohydride as described in example 1 to give 7-[N-3-(4-fluorophenyl)propionyl]amino- I1-N-[ 1,2,3,4-tetrahydro-1-(4-methoxybenzyl)] -6,7-dimethoxyisoquinolinyl]-4,4-diphenylheptane as a film: MS showed (M+H)+ @ 729; 1H-NMR (CDCl3, δ): 1.0-1.22 (m, 4H), 1.91-2.10 (m, 4H), 2.3-2.4 (m, 2H), 2.4-2.85 (m, 6H), 2.85-2.94 (t, 2H), 2.94-3.2 (m, 4H). 3.51-3.67 (m, 1H), 3.55 (s, 31H). 3.76 (s, 3H), 3.82 (s, 3H), 1H. (broad s, 5.13), 5.92 (s, 1H), 6.52 (s, 1H), 6.75-6.97 (m, 6H), 7.07-7.30 (m, 12H); IR (MIC) u 3300, 2950. 1650, 1510 cm-1. The hydrochloride salt was prepared as in example 4 to give 7-[N-3-(4-fluorophenyl)propionyl]-1-[N-(l.2,3,4-tetra- hydro-1-(4-methoxybenzyl)-6,7-dimethoxyisoquinolinyl)]-4,4-diphenylheptane hydrochloride: mp 100-108° C.

Provenance & Evidence