Water → Indole

HRID 2420502Notes

Reaction equation

HRID 2420502 reaction equation
C(C1CCNCC1)(=O)C1C=CC=CC=1.C(N(CC)CC)C.BrCC[C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1.O>CN(C)C=O>[NH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 769243-(2-Bromoethyl)indoleHCID 226102Phenyl(piperidin-4-yl)methanone

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10.4 g of 4-(benzoyl)piperidine, 6.1 g of triethylamine and 11.2 g of 3-(2-bromoethyl)indole in 350 ml of dimethylformamide is stirred at ambient temperature for 16 hours. Water is added dropwise, precipitating an off-white solid. The solid is collected, washed with water and low boiling petroleum ether, and dried. The solid is recrystallized from 95% ethanol to give white flakes, mp [145°-147° C., of 3-]2-(4-benzoylpiperidyl)ethyl]indole.

Workup

  1. customprecipitating an off-white solid
  2. customThe solid is collected
  3. washwashed with water
  4. customdried
  5. customThe solid is recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-316d0639a43041ebac7d9bf02f681a8b
Source dataset
uspto-grants-1978_08
Patent number
US04110459

Reaction notes

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