Diethyl Ether → HCID 68687760, compound

Participants

Reaction Steps

To a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (9.38 g, 0.0509 mol) and N,N-diisopropylethylamine (13.31 mL, 0.0764 mol) in dry dichloromethane (250 mL) at 0° C. under nitrogen was added dropwise a solution of 4-iodo-3-methyl-benzoyl chloride (10.71 g, 0.0382 mol) in dry dichloromethane (30 mL) over ca. 10 minutes. The reaction mixture was allowed to warm slowly to room temperature with stirring over 3 hours then quenched by the addition of water (100 mL). The organic phase was separated, washed with 1 M hydrochloric acid (2×200 mL) and 5% wt/v aqueous sodium carbonate solution (200 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a cream solid. Diethyl ether (150 mL) was added and the resulting suspension stirred vigorously for 3 hours then filtered to afford the title compound (14.73 g, 90%) as a white solid, m.p. 152-153° C.

Provenance & Evidence