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

HRID 325894Notes

Reaction equation

HRID 325894 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-a5aca9cf0f3641539bfeb9dd9b0aa73f
Source dataset
uspto-grants-1984_04
Patent number
US04443443

Reaction notes

Loading…