Ethanol → tert-butyl 4-(3-phenyl-1H-pyrazol-5-yl)piperidine-1-carboxylate

HRID 222250Notes

Reaction equation

HRID 222250 reaction equation
O=[C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=O.O.[NH2:26][NH2:27].C(O)C>C1COCC1>[C:19]1([C:2]2[CH:3]=[C:4]([CH:6]3[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]3)[NH:27][N:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)3×HCID 49760127tert-Butyl 4-(3-oxo-3-phenylpropanoyl)piperidine-1-carboxylate

Product 1

HCID 67109296tert-butyl 4-(3-phenyl-1H-pyrazol-5-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 4-(3-oxo-3-phenylpropanoyl)piperidine-1-carboxylate (3.1 g), hydrazine monohydrate (0.5 mL), ethanol (30 mL), and THF (30 mL) was stirred at room temperature for about 15 hours, and at 60° C. for 1 hour. Hydrazine monohydrate (0.5 mL) was further added thereto, followed by stirring again at 60° C. for 3 hours. Hydrazine monohydrate (4.0 mL) was added thereto again, followed by stirring at 60° C. for 8 hours. After leaving to be cooled, the solvent was evaporated under reduced pressure, and to the residue were added diisopropyl ether and methanol, followed by stirring. The resulting solid was collected by filtration and dried under reduced pressure to obtain tert-butyl 4-(3-phenyl-1H-pyrazol-5-yl)piperidine-1-carboxylate (2.46 g).

Workup

  1. waitat 60° C. for 1 hour
  2. stirringby stirring again at 60° C. for 3 hours
  3. stirringby stirring at 60° C. for 8 hours
  4. customAfter leaving
  5. temperatureto be cooled
  6. customthe solvent was evaporated under reduced pressure
  7. additionto the residue were added diisopropyl ether and methanol
  8. stirringby stirring
  9. filtrationThe resulting solid was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-4edd8abd079f425ab29f50450bbf513d
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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