1,1'-Carbonyldiimidazole → HCID 18621500, compound

Participants

Reaction Steps

A mixture of N-[(3,4-diaminophenoxy)propyl]-1,2,3,4-tetrahydroisoquinoline (200 mg, 0.67 mmol) and CDI (162 mg, 1.0 mmol) in toluene (15 mL) was refluxed for 16 h, then evaporated. The residual solid was washed with EtOAc (2×5 mL) and CHCl3 (5 mL), then dried to give 107 mg (48%) of the title compound as a yellow powder. 1H NMR (DMSO-d6): 1.90-1.96 (m, 2H), 2.591 (d, 2H, J=7), 2.662 (t, 2H, J=5), 2.803 (t, 2H, J=5), 3.560 (s, 2H), 3.967 (t, 2H, J=6), 6.50-6.52 (m, 2H), 6.76-6.80 (m, 1H), 7.05-7.10 (m, 4H), 10.359 (s, 1H), 10.483 (s, 1H). The hydrochloride, mp. 210-5° C. (dec). Analysis, Calcd. for (C19H22ClN3O2+0.3 HCl): C, 61.55, H, 6.06, N, 11.33; Found: C, 61.57, H, 6.14, N, 11.05.

Provenance & Evidence