Hydrazinecarboxaldehyde → 4-(1-Phenyl-1-(2-formylhydrazinocarbonyl)-methylene)piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1394440Notes

Reaction equation

HRID 1394440 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](O)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:45]([NH:47][NH2:48])=[O:46]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:15]([NH:48][NH:47][CH:45]=[O:46])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 12229HydrazinecarboxaldehydeHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 670464544-(1-Phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 670463754-(1-Phenyl-1-(2-formylhydrazinocarbonyl)-methylene)piperidine-1-carboxylic Acid Tert-Butyl EsterYield 124.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(1-phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester (1.05 g, 3.31 mmol), EDCI (0.888 g, 4.63 mmol) and HOBt (0.626 g, 4.63 mmol) in DMF (4 mL) was stirred for 30 min at room temperature and then formic hydrazide (3.97 g, 66.2 mmol) was added. Stirring was continued for 1 h and then the mixture was poured into water and extracted with EtOAc (×3). The combined organic layers were washed (H2O ×3, brine), dried (Na2SO4) and evaporated to give the title compound (1.48 g, 97%) as a colorless oil:

Workup

  1. stirringStirring
  2. waitwas continued for 1 h
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed (H2O ×3, brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-103677e0a53844c2b2bcdfa3e37ad66a
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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