Diisopropylethylamine → 4-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine-1-carbonitrile

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Reaction Steps

Ethyldiisopropylamine (0.96 mL) and bromonitirile (175 mg) are added to a solution of 4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine (400 mg) in dichloromethane (10 mL) and tetrahydrofuran (10 mL), and the reaction mixture is stirred over night at room temperature. Dichloromethane and water are added and the organic phase is separated and washed with water, 10% NH4Cl solution, and brine, and dried over MgSO4. The solvent is evaporated and the residue is triturated with diethyl ether to give a brownish solid. Since this material still contains ethyldiisopropylamine hydrochloride, ethyl acetate and water are added. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. The residue is again triturated with diethyl ether to afford the title compound. LC (method 2): tR=1.18 min; Mass spectrum (ESI+): m/z=383 [M+H]+.

Provenance & Evidence