3-(2-Bromoethyl)indole → Indole

HRID 1389245Notes

Reaction equation

HRID 1389245 reaction equation
BrCC[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.O(CC1CCNCC1)C1C=CC=CC=1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

5

Reactant 3

HCID 769243-(2-Bromoethyl)indoleHCID 81531DiisopropylethylamineHCID 30174444-(Phenoxymethyl)piperidine

Product 1

HCID 798IndoleYield 41%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8.96 g (0.04 mole) of 3-(2-bromoethyl)-indole, 7.65 g (0.04 mole) of 4-phenoxymethylpiperidine, 7.76 g (0.06 mole) of N-ethyl-diisopropylamine and 100 ml of dioxane is heated under reflux for 9 hours. After cooling, the reaction mixture is filtered, the filtrate is evaporated in a vacuum and the residue is taken up in diethy ether, washed with water, dried over anhydrous sodium sulfate and evaporated. After recrystallization from isopropanol/ligroin, there are obtained 5.55 g of 3-[2-(4-phenoxymethyl)-piperidino)-ethyl]-indole (41% of theory); m.p. 113°-114° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 9 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. customthe filtrate is evaporated in a vacuum
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customAfter recrystallization from isopropanol/ligroin, there

Sources & evidence

ORD record
ord-1ca8ad9bd11b4b2f92eaa08bee881ff3
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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