Hydrazine hydrate (1:1) → Ethyl 4-(3-aminopropyl)piperazine-1-carboxylate

HRID 325901Notes

Reaction equation

HRID 325901 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].O.NN>C(O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12802953HCID 12802953, compound

Product 1

HCID 20252224Ethyl 4-(3-aminopropyl)piperazine-1-carboxylateYield 60.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[3-(4-ethoxycarbonyl-1-piperazinyl)propyl]phthalimide (28.9 g) in ethanol (300 ml) was added 100% hydrazine hydrate (8.4 g). The resulting mixture was refluxed with stirring for 4 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. After the addition of an aqueous solution of sodium hydroxide to the residue, 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-ethoxycarbonyl-1-piperazinyl)propylamine (10.9 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
  7. additionAfter the addition of an aqueous solution of sodium hydroxide to the residue
  8. extractionthe mixture was extracted with chloroform The extract
  9. washwas washed with water
  10. dry with materialdried over magnesium sulfate
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9c5870ac485f4be5bcfdd097eaf988d9
Source dataset
uspto-grants-1984_04
Patent number
US04443443

Reaction notes

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