Potassium Carbonate → HCID 86748073, compound

HRID 1742239Notes

Reaction equation

HRID 1742239 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:21][N:22]=[C:23]=[O:24].C(=O)([O-])[O-].[K+].[K+].[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35]>O1CCCC1.C(O)C.C(OC(C)C)(C)C>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[CH3:21][NH:22][C:23](=[O:24])[O:20][C:17]1[CH:16]=[CH:15][C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][N:9]2[CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 444972Fumaric AcidHCID 23361310HCID 23361310, compound

Product 1

HCID 86748073HCID 86748073, compoundYield 57.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{1-[2-(4-morpholinyl)ethyl]-2-pyrrolidinyl}phenol (0.92 g) in dry tetrahydrofuran (50 ml) was added methyl isocyanate (0.22 ml) at ambient temperature, with stirring, over ten mins. Milled potassium carbonate (0.55 g) was added and 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 concentrated. The residue was purified by flash column chromatography (silica gel, 10% methanol/ether). The appropriate fractions were collected and concentrated. The residue was dissolved in dichloromethane and washed with water (5-6 times). The combined aqueous layers were back-extracted with ether, and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated. Fumaric acid (2.02 equivalents) in absolute ethanol and diisopropyl ether was added to the residue to yield (0.55 g, 57.7%) of product, mp 119°-121° 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 concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, 10% methanol/ether)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in dichloromethane
  9. washwashed with water (5-6 times)
  10. extractionThe combined aqueous layers were back-extracted with ether
  11. washthe combined organic extracts were washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-61b2b2fb45414def9658b5e653321a17
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

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