Methanesulfonyl chloride → HCID 89938215, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-hydroxy-4,4-dimethylcyclopent-1-enecarbonitrile (1.5 g, 10.93 mmol) in dichloromethane (20 ml) was added diisopropylethylamine, (5.73 ml, 32.8 mmol) under nitrogen atmosphere. Reaction mixture was cooled to 0-5° C. Methane sulfonyl chloride (1.278 ml, 16.40 mmol) in 2 ml dichloromethane was added drop wise at 0-5° C. in 10 mins. Reaction mixture was stirred at 0-5° C. for 3 h. Progress of reaction was monitored by TLC. Reaction mixture was diluted with dichloromethane (20 ml) and washed with water (2×10 ml), organic layer was dried on sodium sulfate and concentrated under reduced pressure to get sticky compound which was dissolved in dry N,N-dimethylformamide (15 ml) and cooled to 0-5° C. followed by addition of diisopropylethylamine (5.73 ml, 32.8 mmol) and 1-(4-fluorophenyl)piperazine (1.971 g, 10.93 mmol) under nitrogen atmosphere. Reaction mixture was gradually warmed to 25-30° C. and stirring continued for 16 h. Progress of reaction was monitored by TLC. Reaction mixture was concentrated under reduced pressure to obtain crude product which was dissolved in ethyl acetate (100 ml) and washed with water (3×25 ml). Combined organic layer was dried on sodium sulphate and concentrated under reduced pressure to get crude oily product. Crude compound was purified over silica gel (100-200 mesh) by flash column chromatography using 20% ethyl acetate in hexane to obtain title compound (0.260 g).

Provenance & Evidence