Trifluoroacetic acid → 4-benzylpiperidine-4-carboxylic acid N',N'-dimethylhydrazide

HRID 380661Notes

Reaction equation

HRID 380661 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:14]([NH:16][N:17]([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:19][N:17]([CH3:18])[NH:16][C:14]([C:11]1([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 206947194-benzyl-4-(N',N'-dimethylhydrazinocarbonyl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 206947064-benzylpiperidine-4-carboxylic acid N',N'-dimethylhydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzyl-4-(N′,N′-dimethylhydrazinocarbonyl)piperidine-1-carboxylic acid tert-butyl ester (0.76 g, 2.02 mmol) in methylene chloride (2 ml) at 0° C. was added trifluoroacetic acid (5 ml) and the mixture was stirred for 60 min. The mixture was quenched with ethanol (20 ml), concentrated in vacuo and stripped three times with methylene chloride to give 4-benzylpiperidine-4-carboxylic acid N′,N′-dimethylhydrazide in quantitative yield.

Workup

  1. customThe mixture was quenched with ethanol (20 ml)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-007c2015d1e94d4490d8c79d5ede5376
Source dataset
uspto-grants-2001_10
Patent number
US06303620B1

Reaction notes

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