Triethylamine → N-(4-hexadecylamino-2-thiophenecarbonyl)pyrrolidine

HRID 850991Notes

Reaction equation

HRID 850991 reaction equation
C([N:11]([C:28]1[CH:29]=[C:30]([C:33](Cl)=[O:34])[S:31][CH:32]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(OCC1C=CC=CC=1)=O.[CH2:36]([N:38](CC)[CH2:39][CH3:40])[CH3:37].N1CCCC1>CCOCC>[CH2:12]([NH:11][C:28]1[CH:29]=[C:30]([C:33]([N:38]2[CH2:39][CH2:40][CH2:37][CH2:36]2)=[O:34])[S:31][CH:32]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 205036214-[N-(carbobenzyloxy)-N-hexadecylamino]-2-thiophenecarbonyl chloride

Product 1

HCID 20503634N-(4-hexadecylamino-2-thiophenecarbonyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A warm solution of 1.0 g. of 4-[N-(carbobenzyloxy)-N-hexadecylamino]-2-thiophenecarbonyl chloride and 1.3 g. of triethylamine in 100 ml. of ether is added to 1.2 g. of pyrrolidine. A precipitate forms; the mixture is stirred under reflux for 1 hour, filtered, and extracted with hot ether. The extract is evaporated and a solution of the resulting residue in 100 ml. of tetrahydrofuran is shaken under 50 psi of hydrogen in the presence of 0.6 g. of 10% palladium on carbon. The mixture is filtered and the filtrate evaporated. The residue is crystallized from acetic acid to yield the product as a white solid.

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationfiltered
  3. extractionextracted with hot ether
  4. customThe extract is evaporated
  5. stirringof tetrahydrofuran is shaken under 50 psi of hydrogen in the presence of 0.6 g
  6. filtrationThe mixture is filtered
  7. customthe filtrate evaporated
  8. customThe residue is crystallized from acetic acid

Sources & evidence

ORD record
ord-182954555e6c418c85361989a6b34cc9
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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