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

HRID 1284618Notes

Reaction equation

HRID 1284618 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19068116HCID 19068116, compound

Product 1

HCID 31492693-(4-benzylpiperazin-1-yl)propan-1-amineYield 86.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[3-(4-benzyl-1-piperazinyl)propyl]phthalimide (22.4 g) in ethanol (250 m) was added 100% hydrazine hydrate (8.02 g). The resulting mixture was refluxed with stirring for 2.5 hours. The reaction mixture was cooled and then filtered. The filter cake was washed with ethanol. The filtrate and washing were combined and evaporated under reduced pressure. To the residue was added 5% aqueous solution of potassium hydroxide and the mixture was extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and then evaporated under reduced pressure to give an oil of 3-(4-benzyl-1-piperazinyl)propylamine (12.4 g).

Workup

  1. temperatureThe resulting mixture was refluxed
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe filter cake was washed with ethanol
  5. washThe filtrate and washing
  6. customevaporated under reduced pressure
  7. additionTo the residue was added 5% aqueous solution of potassium hydroxide
  8. extractionthe mixture was extracted with chloroform
  9. washThe extract was washed with water
  10. dry with materialdried over magnesium sulfate
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a38a9004cde04c2b8393d7671d332eb1
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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