Dimethyl Sulfate → Butyrophenone, 4'-fluoro-4-(4-(2-methylthiobenzimidazol-1-yl)piperidino)-

HRID 1658296Notes

Reaction equation

HRID 1658296 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]=[C:18]3[SH:26])[CH2:13][CH2:12]2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].S(OC)(O[CH3:35])(=O)=O>O.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]=[C:18]3[S:26][CH3:35])[CH2:15][CH2:16]2)=[O:7])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178520652HCID 178520652, compound

Product 1

HCID 42537Butyrophenone, 4'-fluoro-4-(4-(2-methylthiobenzimidazol-1-yl)piperidino)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

15.9 g of 1-[1-(3-(4-fluorobenzoyl)propyl)-4-piperidyl]-2-mercaptobenzimidazole and 3.2 g of sodium hydroxide were dissolved in a mixture of 24 ml of water and 200 ml of methanol. To the solution, 7.06 g of dimethyl sulfate was added through 4 hours at room temperature (i.e., about 20°-30°C) and then the solution was stirred for an additional 20 minutes. After the reaction, the solution was concentrated and a diluted sodium hydroxide solution was added thereto, followed by extracting with chloroform. The chloroform solution was washed with water, dried and concentrated. The residue was recrystallized from ethanol to give colorless crystals of 1-[1-(3-(4-fluorobenzoyl)-propyl)-4-piperidyl]-2-methylmercaptobenzimidazole having a melting point of 98° to 98.5°C.

Workup

  1. customAfter the reaction
  2. concentrationthe solution was concentrated
  3. additiona diluted sodium hydroxide solution was added
  4. extractionby extracting with chloroform
  5. washThe chloroform solution was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e3e5a53444e94787a4ab3cbafab06c7e
Source dataset
uspto-grants-1976_06
Patent number
US03963727

Reaction notes

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