N-Carbethoxyphthalimide → N-(1-benzylpyrrolidin-3-yl)phthalimide

HRID 975005Notes

Reaction equation

HRID 975005 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.C(OC(N1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])=O)C>ClC>[CH2:7]([N:4]1[CH2:5][CH2:6][CH:2]([N:1]2[C:23](=[O:24])[C:22]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]3[C:20]2=[O:29])[CH2:3]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 27566131-Benzyl-3-aminopyrrolidine

Product 1

HCID 6711061N-(1-benzylpyrrolidin-3-yl)phthalimideYield 73.3%

Reagents, catalysts & solvents 1

HCID 6327Methyl ChlorideSolvent

Procedure

10.0 g of 3-amino-1-benzylpyrrolidine was dissolved into 10 ml of chloromethane, to which 12.4 g of N-ethoxycarbonylphthalimide was added and stirred at a room temperature for 10 hours. The solvent was distilled off, diethyl ether was added and insoluble matters were filtered out. The filtrate was concentrated and purified on silica gel column chromatography, to obtain 12.70 g of the above-captioned compound (yield: 73%)

Workup

  1. additionwas added
  2. distillationThe solvent was distilled off
  3. additiondiethyl ether was added
  4. filtrationinsoluble matters were filtered out
  5. concentrationThe filtrate was concentrated
  6. custompurified on silica gel column chromatography

Sources & evidence

ORD record
ord-132544e9f0484098ab1594f7a0dadfe7
Source dataset
uspto-grants-1997_03
Patent number
US05607953

Reaction notes

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