Dimethylcarbamoyl Chloride → HCID 131720678, compound

HRID 1274448Notes

Reaction equation

HRID 1274448 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12]4([CH2:18][CH2:19][C:5]=3[C:4]=2[CH:3]=1)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]4.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:26][N:27]([CH3:31])[C:28](Cl)=[O:29]>C(#N)C.C(OCC)(=O)C>[OH2:1].[CH3:26][N:27]([CH3:31])[C:28]([O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12]4([CH2:18][CH2:19][C:5]=3[C:4]=2[CH:3]=1)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]4)=[O:29].[CH3:26][N:27]([C:28]([O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12]4([CH2:18][CH2:19][C:5]=3[C:4]=2[CH:3]=1)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]4)=[O:29])[CH3:31]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 10796Cesium carbonateHCID 18915244HCID 18915244, compound

Product 1

HCID 131720678HCID 131720678, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,4-dihydro-7-hydroxy-4-methylspiro[cyclopent[b]indole-3(2H), 4'-piperidine] (0.61 g) and cesium carbonate (1.55 g) in acetonitrile (100 ml) was added dimethylcarbamyl chloride (0.25 g), under nitrogen, with stirring. The reaction mixture was stirred for 24 hrs, diluted with ethyl acetate, and the mixture was washed with saturated sodium chloride solution. The layers were separated, and the organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flash chromatographed (silica), eluting with 5% methanol/dichloromethane. The appropriate fractions were collected and concentrated. The residue was recrystallized from ethyl acetate/petroleum ether. The precipitate was flash chromatographed (silica), eluting with 25% ethyl acetate/dichloromethane to give 0.1 g (15%) of product, mp 110-111° C.

Workup

  1. stirringThe reaction mixture was stirred for 24 hrs
  2. washthe mixture was washed with saturated sodium chloride solution
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customchromatographed (silica)
  8. washeluting with 5% methanol/dichloromethane
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated
  11. customThe residue was recrystallized from ethyl acetate/petroleum ether
  12. customchromatographed (silica)
  13. washeluting with 25% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-64140e5910ed43a197d0a0a8f6c6da22
Source dataset
uspto-grants-2000_12
Patent number
US06156901

Reaction notes

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