Hydrazine hydrate (1:1) → 3-(4-Phenylpiperazin-1-yl)propan-1-amine

HRID 1284630Notes

Reaction equation

HRID 1284630 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][N:16]3C(=O)C4=CC=CC=C4C3=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C>[C:1]1([N:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 64248092-[3-(4-Phenyl-piperazin-1-yl)-propyl]-isoindole-1,3-dione

Product 1

HCID 2612973-(4-Phenylpiperazin-1-yl)propan-1-amineYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[3-(4-phenyl-1-piperazinyl)propyl]phthalimide (18.3 g) in ethanol (300 ml) was added 100% hydrazine hydrate (5.3 g). The resulting mixture was refluxed with stirring for 2 hours. The reaction mixture was evaporated under reduced pressure. After the addition of dil aqueous solution of sodium hydroxide to the residue, the mixture was extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and then evaporated under reduced pressure to give 3-(4-phenyl-1-piperazinyl)propylamine (11.2 g).

Workup

  1. temperatureThe resulting mixture was refluxed
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additionAfter the addition of dil aqueous solution of sodium hydroxide to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ec7a3e0d59884719a71c632f804aaf86
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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