Propylamine → 5-oxo-1-(phenylmethyl)-N-propyl-3-pyrrolidinecarboxamide

HRID 978559Notes

Reaction equation

HRID 978559 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:4]([C:14]([OH:16])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:29]([NH2:32])[CH2:30][CH3:31]>C(#N)C>[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][CH:4]([C:14]([NH:32][CH2:29][CH2:30][CH3:31])=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid

Product 1

HCID 134917985-oxo-1-(phenylmethyl)-N-propyl-3-pyrrolidinecarboxamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 10.96 g (50 mmole) of 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid in 150 ml of acetonitrile was added 9.73 g (60 mmole) of 1,1'-carbonyldiimidazole. The reaction was heated to 60° C., for one hour, cooled to room temperature and treated with 4.13 g (70 mmole) of n-propylamine. After stirring for two hours, the solvent was removed in vacuo and the residue partitioned between ether and water. The organic layer was washed with water, 1N hydrochloric acid, dried over magnesium sulfate, filtered, and evaporated invacuo to give 12.0 g of 5-oxo-1-(phenyl-methyl)-N-propyl-3-pyrrolidinecarboxamide, mp 86°-87° C.

Workup

  1. temperaturecooled to room temperature
  2. customthe solvent was removed in vacuo
  3. customthe residue partitioned between ether and water
  4. washThe organic layer was washed with water, 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated invacuo

Sources & evidence

ORD record
ord-368f19b64f914f0a9ac78ae44a9fa3b1
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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