Hydrazine → N-(2-aminoethyl)-2-(3-methoxyphenyl)pyrrolidine

HRID 742582Notes

Reaction equation

HRID 742582 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:7][CH:8]=1.NN>C(O)C.C(Cl)(Cl)Cl>[NH2:16][CH2:15][CH2:14][N:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 152913732-{2-[2-(3-Methoxyphenyl)-1-pyrrolidinyl]ethyl}-1H-isoindole-1,3(2H) dione

Product 1

HCID 23361315N-(2-aminoethyl)-2-(3-methoxyphenyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2-{2-[2-(3-methoxyphenyl)-1-pyrrolidinyl]ethyl}-1H-isoindole-1,3(2H)dione (0.92 g) in ethanol (30 ml) and chloroform (5 ml) was added anhydrous hydrazine (98%, 0.42 ml) at ambient temperature, under nitrogen. The reaction mixture was warmed under reflux for 1.5 hrs, cooled to ambient temperature, and filtered. The filter cake was washed with ethanol and the combined filtrates were concentrated. The residue was diluted with dichloromethane/ether. The organic solvents were decanted and concentrated to give N-(2-aminoethyl)-2-(3-methoxyphenyl)pyrrolidine.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureunder reflux for 1.5 hrs
  3. filtrationfiltered
  4. washThe filter cake was washed with ethanol
  5. concentrationthe combined filtrates were concentrated
  6. additionThe residue was diluted with dichloromethane/ether
  7. customThe organic solvents were decanted
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a9d9cc1f61414bbea05adc21f3fc766d
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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