Methyl iodide → HCID 18960747, compound

HRID 1708324Notes

Reaction equation

HRID 1708324 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:30]=[CH:29][C:9]([C:10]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21][C:19]3=[O:20])[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1.[C:31](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:31][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:30]=[CH:29][C:9]([C:10]([N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21][C:19]3=[O:20])[CH2:16][CH2:17]2)=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 18960751HCID 18960751, compound

Product 1

HCID 18960747HCID 18960747, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-{1-[4-(2-imidazolyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1.0 g) and potassium carbonate (0.35 g) in dimethylformamide (10 ml) is added methyl iodide (0.16 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. Further, to the mixture are added methyl iodide (0.16 ml) and potassium carbonate (0.3 g), and the mixture is stirred at room temperature for 8 hours. The mixture is poured into ice-water, extracted with ethyl acetate, washed with water and dried over sodium sulfate. After concentrated under reduced pressure, the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=25:1) and recrystallized from ethyl acetate to give 1-{1-[4-(1-methyl-2-imidazolyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.15 g) as colorless scales, m.p. 177°-179° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 8 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationAfter concentrated under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=25:1)
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-65fec4ef612e493f8fbe3114d01082a8
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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