CYCLOHEXYLHYDRAZINE HYDROCHLORIDE
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CYCLOHEXYLHYDRAZINE HYDROCHLORIDE
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CAS No:
24214-73-1
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Formula:
C6H15ClN2
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Chemical Name:
CYCLOHEXYLHYDRAZINE HYDROCHLORIDE
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Synonyms:
CYCLOHEXYLHYDRAZINE HYDROCHLORIDE;1-CYCLOHEXYLHYDRAZINE HYDROCHLORIDE;CyclohexylhydrazineHCl;Hydrazinocyclohexane hydrochloride;Hydrazine, cyclohexyl-,hydrochloride (1:1);Cyclohexylhydrazine hydrochloride 98%;Cyclohexylhydrazine hydrochloride≥ 98%(Titration)
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CAS No:
Characteristics
38
2.67560
White Crystalline Powder
110-114 °C(lit.)
210.9ºC at 760mmHg
91.7ºC
H2O: almost transparency
0.188mmHg at 25°C
CYCLOHEXYLHYDRAZINE HYDROCHLORIDE Use and Manufacturing
General procedure: To a solution of tert-butyl 2-cyclohexylhydrazine-1-carboxylate (1 .9g, 8 .87mmol) in dioxane was added HCl/dioxane (20 mL), it was then refluxed overnight. The white precipitate was filtrated to afford 1.8g (yield:>100percent) of cyclohexylhydrazine hydrochloride as a white solid.To a stirred solution of tert-butyl 2-cyclohexylhydrazinecarboxylate (2.7 g, 1.0 eq) in 40 mL ether was added HC1 (5 mL, 12 N). After addition was completed, the reaction was stirred at r.t. for 3 h. The solvent was removed under reduced pressure. The residue was dissolved in 4 mL EtOH. With stirring 40 mL ether was added. The solid thus formed was collected by filtration, and dried to give the product as a white product (1.6 g, 85percent). ‘H NMR (400 MHz, CDC13) ö2.83-2.88(m, 1H), 1.98-2.00(m, 2H), 1.73-1.74(m, 2H), 1.56-1.60(m, 1H), 1.05-1.27(m, 5H).t-Butylcarboxycyclohexanone hydrazone generated above (40.02 g, 189 mmol) was dissolved in a mixture of 175 mL tetrahydrofuran and 225 mL anhydrous methanol. Sodium cyanoborohydride (Acros, 14.3 g, 227 mmol) was added in portions over ten minutes and the mixture was stirred under argon overnight at room temperature. 135 mL of 6N hydrochloric acid were then added dropwise and the mixture was refluxed for one hour. The reaction was permitted to cool to room temperature and a white solid was removed by filtration. The mother liquor was concentrated and residual water was removed by azeotroping with ethanol on a rotary evaporator (3.x.100 mL). The mixture was concentrated to dryness and was taken up into hot isopropanol (300 mL). The solid that was present was removed by filtration and the mother liquor was concentrated to 1/2 volume at which point an equal volume of ethyl ether was added. This caused cyclohexylhydrazine hydrochloride to precipitate as a white solid. Yield (20.0 g, 93percent).
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CYCLOHEXYLHYDRAZINE HYDROCHLORIDE
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