Hydrazine hydrate (1:1) → 3-[4-(Prop-2-en-1-yl)piperazin-1-yl]propan-1-amine

HRID 1284620Notes

Reaction equation

HRID 1284620 reaction equation
[CH2:1]([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)[CH:2]=[CH2:3].O.NN>C(O)C>[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][NH2:13])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20252233HCID 20252233, compound

Product 1

HCID 202522303-[4-(Prop-2-en-1-yl)piperazin-1-yl]propan-1-amineYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[3-(4-allyl-1-piperazinyl)propyl]phthalimide (35.6 g) in ethanol (400 ml) was added 100% hydrazine hydrate (14.3 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. The residual oil was subjected to column chromatigraphy (aluminum oxide), eluting with a mixture of chloroform and methanol (10:1). The fractions containing the object compound were collected and then evaporated under reduced pressure to give an oil of 3-(4-allyl-1-piperazinyl)propylamine (18.8 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. washeluting with a mixture of chloroform and methanol (10:1)
  8. additionThe fractions containing the object compound
  9. customwere collected
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-015194ee3f7e4bb2a1ee20e2dedd116d
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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