Hydrochloric Acid → HCID 19087479, compound

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Reaction Steps

4-Phenyl-4-(1-piperidino)cyclohexanone of Example 3 (0.95 g, 3.7 mmol) and ammonium acetate (4.3 g, 55 mmole) were dissolved in 30 ml of anhydrous methanol. Sodium cyanoborohydride (0.5 g, 8 mmole) was added to the mixture while stirring. The mixture was stirred at room temperature overnight and concentrated HCl was then added until a white precipitate was obtained. The precipitate was removed by filtration. The filtrate was concentrated under reduced pressure to give a solid residue. The residue was taken up in 100 ml of water and to the aqueous extract was added concentrated HCl to pH 2. The solution was extracted with ethyl ether to remove the unreacted starting material. The mixture was then stirred in an ice bath and sodium hydroxide was added until the solution pH reached 11. The mixture was then extracted with chloroform. The chloroform extract was washed once with water and dried over anhydrous sodium sulfate. Removal of chloroform under reduced pressure gave the desired cyclohexylamine in quantitative yield as a white solid.

Provenance & Evidence