Hydrochloric Acid → 1-(4-fluoro-benzoyl)-(S)-piperidine-3-carboxylic acid hydrazide

HRID 1661180Notes

Reaction equation

HRID 1661180 reaction equation
C(OC([NH:8][NH:9][C:10]([C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:26])[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:13]1)=[O:11])=O)(C)(C)C.Cl>ClCCl>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([N:14]2[CH2:15][CH2:16][CH2:17][C@H:12]([C:10]([NH:9][NH2:8])=[O:11])[CH2:13]2)=[O:26])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66618300N'-[1-(4-fluoro-benzoyl)-(S)-piperidine-3-carbonyl]-hydrazinecarboxylic acid-tert-butyl ester

Product 1

HCID 666184091-(4-fluoro-benzoyl)-(S)-piperidine-3-carboxylic acid hydrazideYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.55 g (1.5 mmol) of N′-[1-(4-fluoro-benzoyl)-(S)-piperidine-3-carbonyl]-hydrazinecarboxylic acid-tert-butyl ester were suspended in 5 mL of dichloromethane and, at 0° C., 4 mL of HCl 4N (dioxane solution) were added. The solution was allowed to warm at room temperature and stirred for 1 h30. The solvent was evaporated under reduced pressure to afford 0.412 g of 1-(4-fluoro-benzoyl)-(S)-piperidine-3-carboxylic acid hydrazide as a white solid extremely igroscopic.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-16b8ecf3363d4888b778e123199be04c
Source dataset
uspto-grants-2011_10
Patent number
US08030331B2

Reaction notes

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