tert-Butyl 4-hydrazinopiperidine-1-carboxylate synthesis

3synthesis methods

Product Name:tert-Butyl 4-hydrazinopiperidine-1-carboxylate
CAS Number:1196486-69-7
Molecular formula:C10H21N3O2
Molecular Weight:215.29

79099-07-3 Synthesis

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tert-Butyl 4-hydrazinopiperidine-1-carboxylate

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Yield: 88%

Reaction Conditions:

Stage #1:N-tert-butyloxycarbonylpiperidin-4-one;hydrazine hydrate in ethanol at 20;Inert atmosphere;
Stage #2: with sodium tetrahydroborate in methanol;ethanol at 0 - 20;

Steps:

9
Intermediate 9: 4-Hydrazino-piperidine-1-carboxylic acid tert-butyl ester; Hydrazine hydrate (100 mL, 2 mol) was added to a solution of 1-Boc-4-piperidone (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 20.0 g, 100 mmol) in ethanol (180 mL) under nitrogen at room temperature and the reaction mixture was stirred at room temperature overnight. Methanol (180 mL) was added and the reaction mixture was cooled to 0-5° C. Sodium borohydride (14.2 g, 375 mmol) was added in portions and the reaction mixture was allowed to warm to room temperature and stir for 2 h. The solvents were evaporated under reduced pressure, dichloromethane was added and the mixture was washed with water, dried (sodium sulfate), filtered, and evaporated to give 4-hydrazino-piperidine-1-carboxylic acid tert-butyl ester (18.9 g, 88%) as a viscous oil, which was used for the next step without further purification.

References:

Location in patent:Page/Page column 21

79099-07-3 Synthesis

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References

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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References