Phenyl chloroformate → HCID 59807140, compound

Participants

Reaction Steps

A solution of N,N-dimethyl-2-(7-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)ethanamine (400 mg, 1.52 mmol) in 10 mL CH2Cl2 was treated dropwise with phenylchloroformate (286 μL, 2.28 mmol). The reaction was stirred at room temperature for 21 hours then partitioned between CH2Cl2 (100 mL) and 1N NaOH (20 mL). After extraction, the organic layer was separated and the aqueous layer was extracted with additional CH2Cl2 (50 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated to give a yellow residue. This residue was subjected to flash chromatography on silica gel using CH2Cl2 to give a yellow residue (460 mg, 82.0%). 1H-NMR (CDCl3) δ 7.99 (dd, J=2.7, 9.0 Hz, 1H), 7.93 (d, J=2.7 Hz, 1H), 7.40-7.34 (m, 2H), 7.23-7.18 (m, 1H), 7.10-7.04 (m, 2H), 6.87 (dd, J=6.3, 2.7 Hz, 1H), 3.65-3.55 (m, 4H), 3.39-3.31 (m, 2H), 3.11 and 3.05 (2×s, 3H), 2.88-2.85 (m, 2H), 1.85-1.65 (m, 4H). MS (ESI): 370.2 (M+1).

Provenance & Evidence