1,2-Dibromoethane → HCID 14459743, compound

Participants

Reaction Conditions

Reaction Steps

In a 1 L three-necked flask, 1,2-dibromoethane (0.3 ml) was added to a refluxing slurry of magnesium chips (4.1 gm) in tetrahydrofuran (80 ml) to initiate a Grignard reaction. A solution of N-methyl-4-chloropiperidine (28 ml) in tetrahydrofuran (30 ml) was added in portions to maintain a fast reflux. The resultant slurry was refluxed for 1 hour and cooled to about 0° C. A solution of 9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (10.0 gm) in tetrahydrofuran (50 ml) was added dropwise. After 1.5 hours of stirring, the mixture was diluted with ethyl acetate (400 ml) and with saturated ammonium chloride solution (600 ml). The organic phase was separated. The aqueous phase was basified with 50% sodium hydroxide solution and then it was extracted twice with ethyl acetate (400 ml). The combined ethyl acetate solution was washed with water (2×300 ml) and brine (2×300 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to a solid.

Provenance & Evidence