Aluminium lithium hydride → 1-benzyl-N,4-dimethylpiperidin-3-amine

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The reduction of cis-(1-benzyl-4-methyl-piperidin-3-yl)-carbamic acid methyl ester was performed by charging 2 grams substrate (1 equiv., 7.62 mmol) to a solution of 20 ml THF (10 volumes) and 15.2 ml 1 M LAH in THF (2 equiv., 15.2 mmol). The addition was performed at a rate so that the temperature reached 30°-40° C. and then the reaction was allowed to cool to 20° C. The reaction was worked up by quenching with 40 ml Rochelle Salt (20 volumes) to a temperature of 35° C. and then extracting the product 2 times into 20 ml methylene chloride (10 volumes). The filtrate was then concentrated to a clear and colorless oil. (90% yield). Note that the starting material needs to be clean in order for this reaction to proceed in high yield.

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