Dimethylcarbamoyl Chloride → Trans-3-(4-chlorophenoxy)-4-hydroxy-N,N-dimethyl-1-pyrrolidinecarboxamide

HRID 1262596Notes

Reaction equation

HRID 1262596 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:11][NH:10][CH2:9][CH:8]2[OH:12])=[CH:4][CH:3]=1.[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[C@H:8]([OH:12])[CH2:9][N:10]([C:17]([N:16]([CH3:20])[CH3:15])=[O:18])[CH2:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 13320209HCID 13320209, compound

Product 1

HCID 13320214Trans-3-(4-chlorophenoxy)-4-hydroxy-N,N-dimethyl-1-pyrrolidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.5 g. of 4-(4-chlorophenoxy)-3-pyrrolidinol, 1.8 g. of dimethylcarbamyl chloride and 1.7 g. of triethylamine in 300 ml of methylene chloride was stirred for 60 hr. The solvent was removed under vacuum, 300 ml of benzene was added and the mixture was refluxed for 2 hr., then filtered. After solvent evaporation, the residue was dissolved in cyclohexane-benzene and charcoaled. The product was then crystallized, collected by filtration and recrystallized from cyclohexane-benzene; m.p. 137°-142° C. Analysis: Calculated for C13H17N2O3Cl: C, 54.84; H, 6.02; N, 9.84. Found: C, 54.64; H, 6.01; N, 9.77.

Workup

  1. customThe solvent was removed under vacuum, 300 ml of benzene
  2. additionwas added
  3. temperaturethe mixture was refluxed for 2 hr
  4. filtration, then filtered
  5. customAfter solvent evaporation
  6. dissolutionthe residue was dissolved in cyclohexane-benzene
  7. customThe product was then crystallized
  8. filtrationcollected by filtration
  9. customrecrystallized from cyclohexane-benzene

Sources & evidence

ORD record
ord-70d73af2ba094f05a6c2b0e7f6c19f4e
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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