Hydrazine hydrate (1:1) → 1-(3-Aminopropyl)-4-methylpiperazine

HRID 1284617Notes

Reaction equation

HRID 1284617 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)[CH2:4][CH2:3]1.O.NN>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][NH2:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 202494272-[3-(4-Methylpiperazin-1-yl)propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 783281-(3-Aminopropyl)-4-methylpiperazineYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[3-(4-methyl-1-piperazinyl)propyl]phthalimide (502 g) in ethanol (3.0 l) was added 100% hydrazine hydrate (187.6 g). The nesulting mixture was refluxed with stiving for 1.5 hours. The reaction mixture was cooled and then filtered. The filter cake was washed with ethanol (1 l). The filtrate and washing were combined and evaporated, under reduced pressure. The residual oil was distilled under reduced pressure to give 3-(4-methyl-1-piperazinyl)propylamine (146.6 g), bp 34 mmHg/127° to 128° C.

Workup

  1. temperatureThe nesulting mixture was refluxed
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe filter cake was washed with ethanol (1 l)
  5. washThe filtrate and washing
  6. customevaporated, under reduced pressure
  7. distillationThe residual oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-90caa7a616664c2881044a1245d3139f
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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