Phenylhydrazine → 1-[beta-(2-Methyl-3-indolyl)propionyl]-4-phenylpiperazine

HRID 1580625Notes

Reaction equation

HRID 1580625 reaction equation
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([CH2:12][CH2:13][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)=[O:16])(=O)[CH3:10]>C(O)(=O)C>[CH3:10][C:9]1[NH:7][C:1]2[C:6]([C:12]=1[CH2:13][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:19][CH2:18]1)=[O:16])=[CH:5][CH:4]=[CH:3][CH:2]=2

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 215633821-(gamma-Acetylbutyryl)-4-phenylpiperazine

Product 1

HCID 215634081-[beta-(2-Methyl-3-indolyl)propionyl]-4-phenylpiperazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 10.8 g of phenylhydrazine in 100 ml of 30 % aqueous acetic acid was added 27.4 g of 1-(γ-acetylbutyryl)-4-phenylpiperazine and the resulting mixture was stirred for 30 minutes at room temperature. The precipitate was filtered, and washed with water. The precipitate was added to 180 ml of 5 % ethanolic hydrogen chloride, and the mixture was heated under reflux for 4 hours. The solvent was distilled off under reduced pressure to the residue, to which was added 100 ml of water. The resulting solid substance was recrystallized from ethanol to give 1-[β-(2-methyl-3-indolyl)propionyl]-4-phenylpiperazine, melting at 120°-121°C.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. additionThe precipitate was added to 180 ml of 5 % ethanolic hydrogen chloride
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 4 hours
  6. distillationThe solvent was distilled off under reduced pressure to the residue, to which
  7. additionwas added 100 ml of water
  8. customThe resulting solid substance was recrystallized from ethanol

Sources & evidence

ORD record
ord-a3f3562bf4ed4ef38fee530db75cd8bb
Source dataset
uspto-grants-1976_01
Patent number
US03933824

Reaction notes

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