Water → 1-Benzoylpiperidine-4-carbohydrazide

HRID 642096Notes

Reaction equation

HRID 642096 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]C)=O)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:20][NH2:21].O>CO>[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([NH:20][NH2:21])=[O:17])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 670253Methyl 1-benzoylpiperidine-4-carboxylate

Product 1

HCID 99648491-Benzoylpiperidine-4-carbohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of (±)-methyl 1-benzoyl-4-piperidinecarboxylate (502 mg, 2.03 mmol) in MeOH (10 mL) was added hydrazine hydrate (1.6 mL). After stirring for 24 h at rt, the reaction mixture and water (40 mL) was added. After washing with Et2O (2×20 mL), the aqueous layer was evaporated off under vacuo. The title compound was obtained as an amorphous beige solid (469 mg, 93%) in a 91.0% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. washAfter washing with Et2O (2×20 mL)
  2. customthe aqueous layer was evaporated off under vacuo

Sources & evidence

ORD record
ord-cabe7a49192943269714bd7fa12a8921
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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