Hydrazine hydrate (1:1) → 1-Pyrrolidinepropanamine

HRID 1861656Notes

Reaction equation

HRID 1861656 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2C(=O)C3=CC=CC=C3C2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>CO>[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12612173HCID 12612173, compound

Product 1

HCID 316701-PyrrolidinepropanamineYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[3-(1-Pyrrolidinyl) propyl] phthalimide (729 mg) and hydrazine monohydrate (284 mg) were dissolved in methanol (9 ml) and the resulting solution was refluxed with heating for 2 hours. After cooling, the reaction solution was concentrated under reduced pressure followed by addition of a 4N sodium hydroxide aqueous solution to the resulting residue and extraction thereof with chloroform. The resulting organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (Reference Compound 2-1, 216 mg).

Workup

  1. temperaturethe resulting solution was refluxed
  2. temperaturewith heating for 2 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. additionfollowed by addition of a 4N sodium hydroxide aqueous solution to the resulting residue and extraction
  6. dry with materialThe resulting organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bfb20f09e8c24a61a333bd72313f3287
Source dataset
uspto-grants-2003_03
Patent number
US06534499B2

Reaction notes

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