Dimethyl Sulfoxide → HCID 10025540, compound

Participants

Reaction Conditions

Reaction Steps

A solution of oxalyl chloride (1.25 g, 0.17 mL, 2.6 mmol) in dichloromethane (5 mL) was cooled to -78°60 C. in a flame dried flask under a nitrogen atmosphere with stirring. A solution of dimethylsulfoxide (0.41 g, 0.37 mL, 5.2 mmol) in dichloromethane (5 mL) was added dropwise; then the reaction mixture was stirred for 15 minutes. A solution of 1-benzyl-4-(2'-(4''-fluorophenyl)hydroxyethyl)piperidine (0.6 g, 2 mmol) in dichloromethane was added dropwise, then the reaction mixture was stirred at -65° to -60° C. for 15 minutes. The mixture was then cooled to -78° C. and triethylamine (0.73 g, 1.0 mL, 7.2 mmol) was added in one portion. The reaction mixture was stirred while being warmed gradually to ambient temperature. After 3 hours, the reaction mixture was poured onto water (100 mL), mixed and extracted three times with ether. The combined organic layers were dried over magnesium sulfate filtered and concentrated in vacuo. Column chromatography (ethyl acetate) gave an oil (588 mg, Rf=0.2):1H-NMR:7.4-6.9(m,9H), 4.65(s,2H), 4.5(s,2H), 3.0-2.9(m,2H), 2.5-2.35(m,1H), 2.1-1.6(m,8H); HR-MS:Calcd for C20H22FNO:311.1700; Found:311.1693.

Provenance & Evidence