N-(1-(2-(3,4-dimethoxyphenyl)ethyl)pyrrolidin-3-yl)phthalimide → 3-Amino-1-(2-(3,4-dimethoxyphenyl)ethyl)pyrrolidine

HRID 975008Notes

Reaction equation

HRID 975008 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH:15]([N:18]3C(=O)C4=CC=CC=C4C3=O)[CH2:14]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>C(O)C.O.NN>[NH2:18][CH:15]1[CH2:16][CH2:17][N:13]([CH2:12][CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14]1

Participants

4

Reactant 1

HCID 15045352N-(1-(2-(3,4-dimethoxyphenyl)ethyl)pyrrolidin-3-yl)phthalimide

Product 1

HCID 150453533-Amino-1-(2-(3,4-dimethoxyphenyl)ethyl)pyrrolidineYield 100.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

1.03 g of N-(1-(2-(3,4-dimethoxyphenyl)ethyl)pyrrolidin-3-yl)phthalimide was dissolved in 50 ml of ethanol, to which 2 ml of hydrazine monohydrate was added and refluxed under heating for 14 hours. The solvent was distilled off and an aqueous diluted solution of sodium hydroxide was added to the residue and extracted with chloroform. After drying with anhydrous magnesium sulfate, the solvent was distilled off, to obtain 0.68 g of the above-captioned compound (yield: 100%).

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. temperatureunder heating for 14 hours
  4. distillationThe solvent was distilled off
  5. additionan aqueous diluted solution of sodium hydroxide was added to the residue
  6. extractionextracted with chloroform
  7. dry with materialAfter drying with anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-b250f5a3ce1b4366a25bd1e78bb20778
Source dataset
uspto-grants-1997_03
Patent number
US05607953

Reaction notes

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