Hydrochloric Acid → 3-Cyclohexanecarbonyl-8-methyl-3,8-diazabicyclo[3.2.1]octane

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Reaction Conditions

Reaction Steps

Cyclohexane carboxylic acid (1.29 g, 0.010 mole) and 1.2 g (0.010 mole) thionyl chloride were heated in a dry atmosphere at 90°C for 1 hour. To this cyclohexane carboxylic acid chloride, at 0°C, was added a mixture of 2.0 g (0.010 mole) 8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (prepared as described in Example 1), 1.6 g sodium hydroxide dissolved in 16 ml water, and 16 ml chloroform which had been stirred vigouously at room temperature and then chilled to 0°C. The reaction was stirred at 0°C for 1 hour. The crude product was isolated as a yellow oil by extraction of the aqueous phase with chloroform. Purification by chromatography on alumina followed by treatment with ethanolic hydrogen chloride yielded 1.58 g (58% yield) of the desired product as a white monohydrochloride, melting point 263°-268°C.

Provenance & Evidence