Methylamine → rac-(1R,2R)-2-(methylamino)cyclohexan-1-ol

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Reaction Steps

Cyclohexene oxide (196.28 g., 2 mole) is added during 30 min. to 40% aqueous methylamine (466 ml., 6 moles) with stirring. The temperature is from 25° to 27° during this addition. During the following 45 min. the temperature rises to 55° and is kept at 50° to 58° by occasional cooling. It is stirred at room temperature for 18 hr., then heated on the steam bath for 2 hrs., cooled and saturated with solid sodium hydroxide (NaOH). The mixture is extracted well with ether, the extract dried over magnesium sulfate (MgSO4) and evaporated through a 9" Vigreux. Distillation at 13 mm gives 241.9 g. (97% yield) of the title compound b.p. 100°-101° nmr in CDCl3 (100 MHz) is in accord; Mass spectrum M+ 129.

Provenance & Evidence