2-(2-Oxopyrrolidin-1-yl)acetic acid → N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-(2-oxo-1-pyrrolidinyl)acetamide

HRID 1904226Notes

Reaction equation

HRID 1904226 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([OH:10])=O.[NH2:11][CH2:12][CH2:13][N:14]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]1[CH3:20]>O1CCCC1>[CH3:20][C:15]1[N:14]([CH2:13][CH2:12][NH:11][C:8](=[O:10])[CH2:7][N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])[C:18]([CH3:19])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 31466872-(2-Oxopyrrolidin-1-yl)acetic acidHCID 137700502-(2,5-Dimethyl-1H-pyrrol-1-yl)ethan-1-amine

Product 1

HCID 13770058N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-(2-oxo-1-pyrrolidinyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

14.3 g (0.1 mol) of (2-oxo-1-pyrrolidinyl)acetic acid and 16.2 g (0.1 mol) of N,N'-carbonyldiimidazole are heated under reflux in 70 ml of tetrahydrofuran for 15 min. After cooling, 13.8 g (0.1 mol) of 1-(2-aminoethyl)-2,5-dimethylpyrrole in 70 ml of tetrahydrofuran are added dropwise. After the reactionmixture has been stirred at room temperature for 6 h, it is concentrated, acifified with dilute acetic acid and extracted with methylene chloride. The methylene chloride extract is concentrated, and the residue is triturated with ether, filtered off with suction and recrystallized from dibuyl ether. Yield: 9.0 g (34% of theory), Melting point: 109°-111° C. Elemental analysis: C14H21N3O2 (263.34) calculated: C 63.9 H 8.0 N 16.0 O 12.2 found: C 63.8 H 8.0 N 15.9 O 12.2

Workup

  1. temperatureAfter cooling
  2. concentrationit is concentrated
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. concentrationis concentrated
  6. customthe residue is triturated with ether
  7. filtrationfiltered off with suction
  8. customrecrystallized from dibuyl ether

Sources & evidence

ORD record
ord-6d0441c2c4d1421bafa2177751c621cd
Source dataset
uspto-grants-1989_06
Patent number
US04837225

Reaction notes

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