Water → HCID 10668025, compound

HRID 974984Notes

Reaction equation

HRID 974984 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[N:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30]I.O>CN(C)C=O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=3)[N:19]=2)[CH3:30])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10667145HCID 10667145, compound

Product 1

HCID 10668025HCID 10668025, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.3 g of 4-{2-[N-(1-benzylpiperid-4-yl)amino]-1,3-thiazol-4-yl}benzonitrile dissolved in 5 ml of N,N-dimethylformamide are added, at room temperature, to 146 mg of sodium hydride (at 60% in dispersion in oil) in suspension in 13 ml of N,N-dimethylformamide and the reaction mixture is stirred for 15 minutes at this temperature. 0.23 ml of methyl iodide is then added, the reaction mixture is stirred for 4 hours at room temperature, and it is poured over water and extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and evaporated. The residue is purified by silica gel chromatography, eluting with dichloromethane. Yellow crystals are obtained which melt at 136° C.; yield: 67%.

Workup

  1. stirringthe reaction mixture is stirred for 4 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with dichloromethane
  8. customYellow crystals are obtained which melt at 136° C.

Sources & evidence

ORD record
ord-e4c55d9ac9bb4a559c9aefa3232a60f1
Source dataset
uspto-grants-1997_03
Patent number
US05607952

Reaction notes

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