Potassium Carbonate → HCID 15222794, compound

HRID 1742233Notes

Reaction equation

HRID 1742233 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:11](=[O:21])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:22][N:23]=[C:24]=[O:25].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:22][NH:23][C:24](=[O:25])[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:9][CH2:10][C:11](=[O:21])[N:12]2[CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 15291371HCID 15291371, compound

Product 1

HCID 15222794HCID 15222794, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-hydroxyphenyl)-1-[2-(4-morpholinyl)ethyl]-2-pyrrolidinone (1.1 g) in dry tetrahydrofuran (50 ml) was added methyl isocyanate (0.26 ml) at ambient temperature, with stirring, over ten mins. Milled potassium carbonate was added, and the reaction mixture was stirred for 17 hrs. The mixture was filtered through a pad of celite. The filter cake was washed with ethyl acetate and the combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, ether/0-50% methanol). The appropriate fractions were collected and concentrated to give 1.2 g (89%) of product. Crystallization of the residue from ether gave the analytical sample, mp 100°-102° C.

Workup

  1. stirringthe reaction mixture was stirred for 17 hrs
  2. filtrationThe mixture was filtered through a pad of celite
  3. washThe filter cake was washed with ethyl acetate
  4. concentrationthe combined filtrates were concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, ether/0-50% methanol)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8661bbdb4a2d437a8a75e1aa098ea4ee
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

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