Hydrochloric Acid → Bicyclo[3.1.1]heptane-3-methanamine, 2,6,6-trimethyl-, hydrochloride (1:1)

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Reaction Steps

300 g of ethanol and 50 g of Raney cobalt are introduced into a high pressure vessel of 2.5 liters capacity and the air is flushed out with nitrogen. The reaction mixture is then heated to 80° C and placed under a hydrogen pressure of 150 atmospheres. 200 g of (+)-3-formylpinane are introduced in the course of 6 hours and after a further 2 hours the reaction mixture is cooled and the pressure is released. 650 g of a mixture are obtained; its fractional distillation gives 106 g of (+)-3-aminomethylpinane boiling at from 110° to 111° C/20 mm Hg. 120 g of the 3-aminomethylpinane are dissolved in 1.3 l of pentane and dry hydrogen chloride is passed into the solution at from 0° to 5° C, whilst stirring. When free amine is no longer detectable the crystals produced are filtered off and dried. 142 g of (+)-3-aminomethylpinane hydrochloride of optical rotation [α]D23 = + 35.4° (c = 1, methanol) are obtained.

Provenance & Evidence