Dichloromethane → HCID 58494891, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of benzazepine hydrochloride (5.0 g, 27.2 mmol) in DCM (˜50 ml) diisopropyl ethylamine (10.4 ml, 59.8 mmol) was added at 0° C., followed by dropwise addition of ethyl chloroformate (2.86 ml, 29.9 mmol). The reaction was stirred at 0° C. for 1 hour and then allowed to warm to room temperature over 2 hours. LCMS indicated reaction was complete, and 1N HCl (˜100 ml) was added to the reaction. The layers were separated and the aqueous layer was extracted with additional DCM (2×). The combined DCM extracts were washed with brine and dried over Na2SO4. The solvent was evaporated in vacuo and the residue purified by silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexanes) to provide the sub-title product as an oil (5.5 g). 1HNMR (CDCl3) δ 7.14 (s, 4H), 4.18 (q, J=7.2 Hz, 2H), 3.61 (bs, 4H), 2.92 (bs, 4H), 1.29 (t, J=7.2 Hz, 3H); MS: ESI (positive): 220 (M+H).

Provenance & Evidence