1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86621468, compound

Participants

Reaction Conditions

Reaction Steps

Trans-2-(4-chlorophenyl)cyclopropanamine hydrochloride (see Bioorganic and Medical Chemistry 12(9), 2021-2034, 2004) (628 mg, 3.08 mmol) was suspended in dry dichloromethane (15 ml) and cooled to 0° C. with stirring under argon. 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.40 g, 9.225 mmol) was added, followed by the dropwise addition of isopropylsulfonyl chloride (877 mg, 6.15 mmol) with stirring under an atmosphere of argon. The reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was then washed with 1 N HCl (2×50 ml). The organic layer was dried over sodium sulphate and evaporated in vacuo to give a yellow oil. The crude product was chromatographed on a 5 g isolute silica Sep-Pak® column eluting from 0-50% ethyl acetate in petroleum ether to give the title compound (570 mg, 68%); mass spectrum (API−): Found 272 (MH−);

Provenance & Evidence