2-phenylmalonaldehyde → HCID 58270702, compound

HRID 222251Notes

Reaction equation

HRID 222251 reaction equation
[NH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)[NH2:2].[C:16]1([CH:22]([CH:25]=O)[CH:23]=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:16]1([C:22]2[CH:23]=[N:2][N:1]([CH:3]3[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]3)[CH:25]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 36722962-phenylmalonaldehydeHCID 56965816HCID 56965816, compound

Product 1

HCID 58270702HCID 58270702, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl 4-hydrazinopiperidine-1-carboxylate (646 mg) and ethanol (15 mL) was added phenyl malonaldehyde (444 mg), followed by stirring at 75° C. for about 1.5 days. The reaction liquid was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/chloroform-50/50 to 0/100) to obtain tert-butyl 4-(4-phenyl-1H-pyrazol-1-yl)piperidine-1-carboxylate (226 mg).

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/chloroform-50/50 to 0/100)

Sources & evidence

ORD record
ord-94da3a97fd0a4539afa0695ad30dae21
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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