Sodium Cyanide → HCID 18431538, compound

Participants

Reaction Conditions

Reaction Steps

24.9 (69.2 mmol) 4-(1-diphenylmethyl-piperidin-4-yl)-butan-1-ol hydrochloride are suspended in 160 ml absolute dichloromethane and cooled to ca. 0° C. under moisture exclusion. At this temperature, 16.0 g (159 mmol) TEA are first added and thereafter a solution of 0.3 g (90.0 mmol) methanesulfonoic acid chloride in a little absolute dichloromethane is added dropwise. The mixture is then subsequently stirred for three hours at RT and then placed in ice water. The organic phase is washed once with 50 ml water, dried over sodium sulfate and the solvent is removed under vacuum. The resulting methanesulfonoic acid-4-(1-diphenylmethyl-piperidin-4-yl)-butyl ester is dissolved in 120 ml DMF without further purification and with 7.7 g (158 mmol) sodium cyanide and two drops 15-crown-5 and stirred for six hours at 65° C. After cooling, the mixture is poured in ice water. The precipitated solid is drawn off and dried at 40° C. in high-vacuum. The solid is processed further without additional purification. Yield: 19.9 g (86%).

Provenance & Evidence