Cyclopentylamine → Methyl 3-(cyclopentylamino)propanoate

HRID 2111239Notes

Reaction equation

HRID 2111239 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([O:11][CH3:12])(=[O:10])[CH:8]=[CH2:9]>CO>[CH3:12][O:11][C:7](=[O:10])[CH2:8][CH2:9][NH:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 7294Methyl Acrylate

Product 1

HCID 28307099Methyl 3-(cyclopentylamino)propanoateYield 64.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 59.605 g (0.70 mole) cyclopentylamine (Aldrich), 72.299 g (0.84 mole) of methyl acrylate (Aldrich) and 250 mL of methanol was heated at reflux under an argon atmosphere for 14 hours, then ca 200 mL of solvent was distilled out at atmospheric pressure. The residue was distilled under vacuum (12 mm Hg, bp 112-114 degrees) to give 77.616 g (64%) of 3-cyclopentylamino-propanoic acid methyl ester.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an argon atmosphere for 14 hours
  3. distillationca 200 mL of solvent was distilled out at atmospheric pressure
  4. distillationThe residue was distilled under vacuum (12 mm Hg, bp 112-114 degrees)

Sources & evidence

ORD record
ord-36a44ca9bffc46d7831bf4262ea08eaf
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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