Hydrochloric Acid → 1-Cyclohexyl-1-methylhydrazine

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Reaction Steps

To a solution of N-methylcyclohexylamine (17 g) in a 6N aqueous hydrochloric acid solution (90 ml) is added dropwise an aqueous solution (60 ml) of sodium nitrite (20.7 g) at 60° C. The mixture is stirred at the same temperature for 2 hours, and diluted with methanol (300 ml). To the mixture are added an aqueous solution (100 ml) of sodium hydroxide (45 g) and formamidine sulfinic acid (39 g). The mixture is refluxed for 2 hours, and diluted with water (400 ml). The mixture is extracted three times with methylene chloride, and the extract is washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent. The residue is distilled under reduced pressure to give 1-methyl-1-cyclohexylhydrazine (10 g) as a colorless oil.

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