Potassium Carbonate → HCID 15291372, compound

HRID 742567Notes

Reaction equation

HRID 742567 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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][C:5]([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:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 23361283HCID 23361283, compound

Product 1

HCID 15291372HCID 15291372, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-hydroxyphenyl)-1-[2-(4-morpholinyl)ethyl]pyrrolidin-2-one (0.99 g) in dry tetrahydrofuran (50 ml) was added methyl isocyanate (0.22 ml) at ambient temperature, with stirring, over ten mins. Milled potassium carbonate (0.565 g) was added, the reaction mixture was stirred for 2 days and 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, 1% triethylamine/1-10% methanol/ether) and (silica gel, 5% methanol/ether). The appropriate fractions were collected and concentrated to afford 0.62 g (52.3%) of product. Recrystallization from absolute ethanol/ether gave the analytical sample, mp 119°-120° C.

Workup

  1. stirringthe reaction mixture was stirred for 2 days
  2. filtrationfiltered 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, 1% triethylamine/1-10% methanol/ether) and (silica gel, 5% methanol/ether)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e04841a938cf4673ac13ecbf865570ca
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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