1,1'-Carbonyldiimidazole → HCID 59608067, compound

HRID 980711Notes

Reaction equation

HRID 980711 reaction equation
O=[C:2]1[N:6](CC2C=CC=CC=2)[CH2:5][CH:4]([C:14]([OH:16])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:29]1([NH2:32])[CH2:31][CH2:30]1>C(#N)C>[CH:29]1([NH:32][C:14]([CH:4]2[CH2:3][CH2:2][NH:6][CH2:5]2)=[O:16])[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 69828CyclopropylamineHCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid

Product 1

HCID 59608067HCID 59608067, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 16.4 g (75 mmole) of 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid in 150 ml of acetonitrile was added 13.8 g (85 mmole) of 1,1'-carbonyldiimidazole. The reaction was heated to 60° C. for one hour, cooled to room temperature and treated with 4.85 g (85 mmole) of cyclopropylamine. The reaction was stirred at room temperature for 18 hours, the solvent removed in vacuo and the residue partitioned between chloroform and water. The organic layer was washed with water, 1 N hydrochloric acid, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 18.3 g of 5-oxo-1-phenylmethyl)-N-cyclopropyl-3-pyrrolidinecarboxamide, mp 94°-96° C.

Workup

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

Sources & evidence

ORD record
ord-064ce4c4f4194daab1b51398bbcb6806
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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