Potassium Carbonate → 3-{1-[2-[(4-Chlorobenzoyl)amino]ethyl]-2-pyrrolidinyl}phenyl methylcarbamate

HRID 233038Notes

Reaction equation

HRID 233038 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:25][N:26]=[C:27]=[O:28].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:25][NH:26][C:27](=[O:28])[O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH:12]2[CH2:13][CH2:14][CH2:15][N:11]2[CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:24][CH:23]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 233612984-chloro-N-{2-[2-(3-hydroxyphenyl)-1-pyrrolidinyl]ethyl}benzamide

Product 1

HCID 152227993-{1-[2-[(4-Chlorobenzoyl)amino]ethyl]-2-pyrrolidinyl}phenyl methylcarbamateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 4-chloro-N-{2-[2-(3-hydroxyphenyl)-1-pyrrolidinyl]ethyl}benzamide (0.29 g) was dissolved in tetrahydrofuran (20 ml), and methyl isocyanate (50.0 μl) and milled potassium carbonate (0.17 g) at ambient temperature were added, under nitrogen. The reaction mixture was stirred for 2 hrs and filtered through a pad of celite. The filter cake was washed with ethyl acetate, and the combined filtrates were concentrated. Crystallization of the residue with ether/petroleum ether gave 0.32 g (94%) of product. Recrystallization from ether gave the analytical sample, mp 103°-106° C.

Workup

  1. additionwere added, under nitrogen
  2. filtrationfiltered through a pad of celite
  3. washThe filter cake was washed with ethyl acetate
  4. concentrationthe combined filtrates were concentrated
  5. customCrystallization of the residue with ether/petroleum ether

Sources & evidence

ORD record
ord-e78587a8432e4a7aa54a98a39abe16f4
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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