Water → HCID 14053219, compound

HRID 1252506Notes

Reaction equation

HRID 1252506 reaction equation
[CH3:1][C:2]1[C:3]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][C:5]([CH2:8][S:9][C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:6][CH:7]=1.[OH-].[K+].[CH3:27]I.O>CS(C)=O>[CH3:27][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[C:10]1[S:9][CH2:8][C:5]1[CH:4]=[C:3]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:2]([CH3:1])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 14053215HCID 14053215, compound

Product 1

HCID 14053219HCID 14053219, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-[(5-Methyl-4-piperidino-2-pyridyl)methylthio]indole (80 mg, 0.24 mmol) was added to a suspension of potassium hydroxide (finely ground) (62 mg) in dimethylsulfoxide (0.5 ml), and the mixture was stirred for 30 minutes. Methyl iodide (34 mg, 0.24 mmol) was then added to the mixture and the stirring was continued at room temperature for further 30 minutes. Then, water (20 ml) was added to the reaction solution and the mixture was extracted with ethyl ether. The ether layer so separated was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography (eluent: chloroform), yielding the titled compound (75 mg) as an oil. Yield: 90%.

Workup

  1. waitthe stirring was continued at room temperature for further 30 minutes
  2. extractionthe mixture was extracted with ethyl ether
  3. customThe ether layer so separated
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-93e8f95309c74f6f97c2855891270dc0
Source dataset
uspto-grants-1988_05
Patent number
US04743609

Reaction notes

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