Phenylacetaldehyde → (6-Phenethylaminohexyl)-carbamic acid tert-butyl ester

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Reaction Steps

(6-Aminohexyl)carbamic acid tert-butyl ester hydrochloride (5 g, 20 mmol) was dissolved in 50% dichloromethane/methanol (50 mL) and treated at ambient temperature with phenylacetaldehyde (2.3 mL, 20 mmol) for one hour. Sodium cyanoborohydride (1.2 g, 19 mmol) was added and the mixture stirred overnight. Water was added, followed by saturated sodium hydrogencarbonate and additional dichloromethane. The mixture was partitioned, the organics dried over sodium sulfate and the volatiles removed under reduced pressure to give the title intermediate, which was used without further purification.

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