Diethyl Ether → HCID 22645406, compound

Participants

Reaction Steps

To a stirred solution of 1-hexyl-3,4-dimethyl-4-(3-cyanophenyl)piperidine (Example 1, 800 mg, 2.68 mmol) in anhydrous tetrahydrofuran (40 mL) at 0° C. under nitrogen was added lithium aluminium hydride (1.0 M in tetrahydrofuran, 4.0 mL, 4.0 mmol). The reaction mixture was allowed to warm to room temperature, before being heated to 37° C. for 30 minutes. Subsequently, diethyl ether (50 mL), then aqueous sodium hydroxide (0.3 mL, 15% w/v solution) and finally water (0.45 mL) were added. The white solid formed was filtered off. The filtrate was washed with saturated aqueous sodium hydrogencarbonate solution (2×50 mL). The aqueous phases were back-extracted with diethyl ether (50 mL). The combined organics were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil (770 mg).

Provenance & Evidence