Dicyclohexylcarbodiimide → HCID 53665932, compound

Participants

Reaction Steps

Dicyclohexylcarbodiimide (0.506 g) in dichloromethane (10 mL) is added to (R)-3-phenyl-3-cyclohexenecarboxylic acid (0.414 g, Example D), 2-pyridylpiperazine (0.410 g) and hydroxybenzotriazole hydrate (0.332 g) in dichloromethane (40 mL) and stirred overnight. The mixture is filtered and evaporated. The residue is dissolved in ethyl acetate, filtered, washed with saturated sodium bicarbonate, 5% citric acid, 2N sodium carbonate, brine, dried over magnesium sulfate, filtered, and evaporated to leave a yellow solid. This solid is dissolved in tetrahydrofuran (5 mL) and added to lithium aluminum hydride (78 mg) in tetrahydrofuran (5 mL) pretreated with aluminum chloride (90 mg) in ether (5 mL) at 0° C. and stirred for 2 hours. Water (0.1 mL) and 25% sodium hydroxide (0.4 mL) are added and the mixture filtered, washed with brine, dried over magnesium sulfate, filtered, and evaporated to a yellow oil. This oil is purified by medium pressure liquid chromatography on silica gel eluting with 50% ethyl acetate in hexane to give 0.22 g of (R)-1-[(3-Phenyl-3-cyclohexen-1-yl)methyl]-4-(2-pyridinyl)piperazine as an off-white solid; mp 106°-108° C.

Provenance & Evidence