Hydrazine hydrate (1:1) → 3-(4-Isopropyl-piperazin-1-yl)-propylamine

HRID 1284627Notes

Reaction equation

HRID 1284627 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][N:13]2C(=O)C3=CC=CC=C3C2=O)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].O.NN>C(O)C>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([CH2:10][CH2:11][CH2:12][NH2:13])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20252235N-[3-(4-isopropyl-1-piperazinyl)propyl]phthalimide

Product 1

HCID 128029563-(4-Isopropyl-piperazin-1-yl)-propylamineYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[3-(4-isopropyl-1-piperazinyl)propyl]phthalimide (43.1 g) in ethanol (350 ml) was added 100% hydrazine hydrate (11.2 g). The resulting mixture was refluxed with stirring for 3 hours. The reaction mixture was cooled and then filtered. The filter cake was washed with ethanol. The filtrate and washing were combined and concentrated under reduced pressure. The residual oil was subjected to column chromatography (aluminum oxide), eluting with a mixture of chloroform and methanol (20:1). The fractions containing the object compound were collected and then evaporated under reduced pressure. The residual oil was distilled under reduced pressure to give 3-(4-isopropyl-1-piperazinyl)propylamine (15.0 g), (bp 45 mmHg/150° C.).

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. concentrationconcentrated under reduced pressure
  7. washeluting with a mixture of chloroform and methanol (20:1)
  8. additionThe fractions containing the object compound
  9. customwere collected
  10. customevaporated under reduced pressure
  11. distillationThe residual oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-de84a78453be4cba959090a31cb1c7f4
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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