ChemicalBook CAS DataBase List Cyclopentylhydrazine hydrochloride

Cyclopentylhydrazine hydrochloride synthesis

6synthesis methods

Product Name:Cyclopentylhydrazine hydrochloride
CAS Number:24214-72-0
Molecular formula:C5H13ClN2
Molecular Weight:136.62

Hydrazinecarboxylic acid, cyclopentylidene-, 1,1-dimethylethyl ester (9CI)

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Yield:24214-72-0 100%

Reaction Conditions:

Stage #1: tert-butyl 2-cyclopentylidenehydrazine carboxylatewith sodium cyanoborohydride in tetrahydrofuran;methanol; for 0.166667 h;Heating / reflux;
Stage #2: with hydrogenchloride in tetrahydrofuran;methanol;water at 20; for 4.5 h;Heating / reflux;

Steps:

64.2

Step 2: Cyclopentyl-hydrazine hydrochloride N'-Cyclopentyl-hydrazinecarboxylic acid tert-butyl ester (5.448 g, 27.48 mmol) was dissolved in dry tetrahydrofuran (25 mL) and dry methanol (34 mL). Sodium cyanoborohydride (2.044 g, 32.53 mmol) was added portionwise and then the mixture was refluxed under argon for 10 minutes. After cooling to room temperature, 6N HCl (12 mL) was added and the mixture was refluxed for 1.5 hours. The NMR of an aliquot at this time showed some BOC-protected material to still be present. Additional 6N HCl was added and the mixture was refluxed for another 3 hours and then cooled to room temperature and stirred overnight. The mixture was filtered to remove the insoluble material, concentrated and azeotroped three times with toluene to remove the water. The residue was dissolved in hot isopropanol, cooled to room temperature, diluted with ether and chilled. Filtration yielded cyclopentyl-hydrazine hydrochloride (3.903 g, 103%) which was used without any further purification.

References:

US2007/225280,2007,A1 Location in patent:Page/Page column 48

646071-31-0 Synthesis