Water → HCID 19048710, compound

HRID 1779917Notes

Reaction equation

HRID 1779917 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[C:8]([CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)=[O:9].CS(O[CH2:22][CH2:23][C:24]1[CH:28]=[CH:27][S:26][CH:25]=1)(=O)=O.O>CN(C)C=O>[CH3:16][N:13]1[CH2:14][CH2:15][CH:10]([C:8]([C:4]2[N:3]([CH2:22][CH2:23][C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)[CH:7]=[CH:6][N:5]=2)=[O:9])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11356008HCID 11356008, compoundHCID 144229343-Thiopheneethanol methanesulfonate

Product 1

HCID 19048710HCID 19048710, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A dispersion of sodium hydride in mineral oil (50%) (0.088 mol) was added portionwise in N,N-dimethylformamide (150 ml) under nitrogen with stirring. (1H-imidazol-2-yl)-(1-methyl-4-piperidinyl)methanone (0.08 mol) was added portionwise and the mixture was stirred for 1 hour. 3-Thiopheneethanol methanesulfonate (ester) (0.086 mol) dissolved in a little N,N-dimethylformamide was added dropwise and the mixture was stirred on an oil bath at 60° C. overnight. The mixture was cooled, decomposed with water and extracted with dichloromethane. The organic layer was dried, filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3)95/5). The pure fractions were collected and evaporated, yielding 15 g (61.8%) of (1-methyl-4-piperidinyl)[1-[2-(3-thienyl)ethyl]-1H-imidazol-2-yl]methanone (interm. 8).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. additionwas added dropwise
  3. stirringthe mixture was stirred on an oil bath at 60° C. overnight
  4. temperatureThe mixture was cooled
  5. extractionextracted with dichloromethane
  6. customThe organic layer was dried
  7. filtrationfiltered off
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3)95/5)
  10. customThe pure fractions were collected
  11. customevaporated

Sources & evidence

ORD record
ord-2e3feba67af74953a742d95336a2facf
Source dataset
uspto-grants-1997_05
Patent number
US05629308

Reaction notes

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