Pyridine → 5-Oxo-2-pyrrolidine carboxylic acid n-dodecylamide

HRID 1605033Notes

Reaction equation

HRID 1605033 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].N1C=CC=CC=1.[O:20]=[C:21]1[NH:25][CH:24]([C:26](Cl)=[O:27])[CH2:23][CH2:22]1>O>[CH2:1]([NH:13][C:26]([CH:24]1[CH2:23][CH2:22][C:21](=[O:20])[NH:25]1)=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13583DodecylamineHCID 123788552-Pyrrolidinecarbonyl chloride, 5-oxo-

Product 1

HCID 542276525-Oxo-2-pyrrolidine carboxylic acid n-dodecylamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While cooling and stirring a mixture consisting of 9.2 gm (0.05 mol) of n-dodecylamine and 50 ml of pyridine, 17.3 gm (0.05 mol) of 5-oxo-2-pyrrolidine carboxylic acid chloride were added thereto in small portions, and the resulting mixture was stirred for one hour at room temperature. Thereafter, the reaction mixture was admixed with water, acidified and extracted with chloroform. The organic phase was separated, washed with water, dried and evaporated. The residue was recrystallized from ethyl acetate, yielding 9.0 gm (62% of theory) of the compound of the formula ##EQU5## which had a melting point of 114°-116°C.

Workup

  1. temperatureWhile cooling
  2. additionwere added
  3. stirringin small portions, and the resulting mixture was stirred for one hour at room temperature
  4. extractionextracted with chloroform
  5. customThe organic phase was separated
  6. washwashed with water
  7. customdried
  8. customevaporated
  9. customThe residue was recrystallized from ethyl acetate
  10. customyielding 9.0 gm (62% of theory) of the compound of the formula ##EQU5## which

Sources & evidence

ORD record
ord-6941d11eada34d89840948d315ea7f87
Source dataset
uspto-grants-1976_04
Patent number
US03948943

Reaction notes

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