Water → HCID 69412619, compound

HRID 457782Notes

Reaction equation

HRID 457782 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].CS(O[CH2:28][CH2:29][C:30]1[CH:34]=[CH:33][S:32][CH:31]=1)(=O)=O.O>CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:28][CH2:29][C:30]3[CH:34]=[CH:33][S:32][CH:31]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11380267Ethyl 4-(1H-indol-3-yl)piperidine-1-carboxylateHCID 144229343-Thiopheneethanol methanesulfonate

Product 1

HCID 69412619HCID 69412619, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Under inert atmosphere, a solution of 6.9 g (0.025 mol) of 4-(1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester in 25 mL of anhydrous DMF was added dropwise to a suspension containing 1.2 g (0.030 mol) of sodium hydride (60% in mineral oil) in 70 mL of anhydrous DMF. After stirring at room temperature for 1 hour, a solution of 6.2 g (0.03 mol) of 2-thiophen-3-yl-ethyl methansulfonate in 15 mL of anhydrous DMF was added. The reaction mixture was stirred at room temperature for 30 minutes and then heated at 60° for 3 hours. The crude mixture was poured into water and extracted with dichloromethane. After drying, the solvent was removed under reduced pressure and 10.3 g of a crude oil were obtained. The crude mixture was purified by flash chromatography over silica gel affording 8.3 g (86% of yield) of the expected product.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. temperatureheated at 60° for 3 hours
  3. extractionextracted with dichloromethane
  4. customAfter drying
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2105d2cf56f048c99a3d0a917d136c7f
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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