Water → 3-{2-[4-(4-Hydroxybenzoyl)piperidyl]ethyl}indole

HRID 867008Notes

Reaction equation

HRID 867008 reaction equation
Br.[OH:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].Br[CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1.O>CS(C)=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:11][CH2:10]2)=[O:8])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 769243-(2-Bromoethyl)indoleHCID 516892Sodium BicarbonateHCID 203116904-(4-Hydroxybenzoyl)piperidine hydrobromide

Product 1

HCID 131802853-{2-[4-(4-Hydroxybenzoyl)piperidyl]ethyl}indole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 9.7 g of 4-(4-hydroxybenzoyl)piperidine hydrobromide, 6.4 g of sodium bicarbonate and 7.0 g of 3-(2-bromoethyl)indole in 90 ml of dimethylsulfoxide is stirred overnight under nitrogen at 50° C. After cooling to ambient temperature, water is added dropwise, precipitating a gummy brown solid. The supernatant solution is decanted from the solid, triturated with water, collected, and dried. Recrystallization from an ethanol-water mixture gives an off-white solid, mp 212°-214° C. (dec.) of 3-{2-[4-(4-hydroxybenzoyl)piperidyl]ethyl}indole.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customprecipitating a gummy brown solid
  3. customThe supernatant solution is decanted from the solid
  4. customtriturated with water
  5. customcollected
  6. customdried
  7. customRecrystallization from an ethanol-water mixture

Sources & evidence

ORD record
ord-24c4c7182dff4541bfc03d91bb888071
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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