Sodium Hydroxide → 2-(3-Cyano-3,3-diphenylpropyl)piperidine

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Reaction Steps

1-Benzyl-2-(3-cyano-3,3-diphenylpropyl)piperidine oxalate (3.70 g, 7.5 mmol--see Example 25) was partitioned between ethyl acetate and 0.5M aqueous sodium hydroxide solution and the organic layer was dried over magnesium sulphate and evaporated. The residue was dissolved in a mixture of acetic acid (5 ml), ethanol (5 ml) and water (2 ml) and the solution treated with sodium acetate (100 mg), palladium dichloride (100 mg) and charcoal. The mixture was stirred under 4 atmospheres of hydrogen at room temperature for 26 hours, filtered and evaporated. The residue was partitioned between ethyl acetate and 10% aqueous sodium carbonate solution and the organic layer was washed with water, dried over magnesium sulphate and evaporated to give the title compound (2.0 g, 88%) as a colourless oil which was characterised by its 1H-NMR spectrum.

Provenance & Evidence