Isopropanol → 1h-Indole,3-[2-[4-(4-bromophenoxy)-1-piperidinyl]ethyl]-

HRID 437566Notes

Reaction equation

HRID 437566 reaction equation
Cl.[Br:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(C)C.Br[CH2:27][CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1>C1C=CC=CC=1>[Br:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([CH2:27][CH2:28][C:29]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[NH:31][CH:30]=3)[CH2:12][CH2:13]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 3776Isopropanol2×HCID 11430Potassium CarbonateHCID 769243-(2-Bromoethyl)indoleHCID 214286994-(4-Bromophenoxy)piperidine hydrochloride

Product 1

HCID 541811811h-Indole,3-[2-[4-(4-bromophenoxy)-1-piperidinyl]ethyl]-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 8.1 g of 4-(p-bromophenoxy)piperidine hydrochloride, 12.6 g of potassium carbonate and 60 ml. of isopropanol is stirred and refluxed for one hour. A solution of 6.5 g of 3-(2-bromoethyl)indole in 15 ml. of isopropanol is then added. Stirring and refluxing is continued for 22 hours, and the reaction mixture is filtered hot. A yellow oil separates in the cooled filtrate and the supernatant isopropanol is decanted from the oil. The isopropanol is diluted with ether, causing the unreacted 4-(p-bromophenoxy)piperidine to separate. After filtration, the isopropanol is removed under reduced pressure to give a yellow oil. The oil is permitted to stand for 3 weeks during which time it solidifies to a soft brown solid. Trituration of the solid with benzene affords yellow crystals, which are recrystallized from acetonitrite to give slightly yellow cubes of 3-{2-[4-(p-bromophenoxy)piperidyl]ethyl]-indole, m.p. 132°-134° C.

Workup

  1. temperaturerefluxed for one hour
  2. temperaturerefluxing
  3. filtrationthe reaction mixture is filtered hot
  4. customA yellow oil separates in the cooled filtrate and the supernatant isopropanol is decanted from the oil
  5. additionThe isopropanol is diluted with ether
  6. customto separate
  7. filtrationAfter filtration
  8. customthe isopropanol is removed under reduced pressure
  9. customto give a yellow oil
  10. waitto stand for 3 weeks during which time it
  11. customare recrystallized from acetonitrite

Sources & evidence

ORD record
ord-8ee138155fce4b838b3f735eca8f4150
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

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