2-Bromoethanol → 4-(1H-indol-1-yl)-1-piperidineethanol

HRID 580898Notes

Reaction equation

HRID 580898 reaction equation
Br[CH2:2][CH2:3][OH:4].[NH:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)[CH2:7][CH2:6]1.C(=O)([O-])O.[Na+]>C(O)C>[N:11]1([CH:8]2[CH2:9][CH2:10][N:5]([CH2:2][CH2:3][OH:4])[CH2:6][CH2:7]2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 516892Sodium BicarbonateHCID 140907551-(Piperidin-4-yl)-1H-indole

Product 1

HCID 538482484-(1H-indol-1-yl)-1-piperidineethanolYield 65.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromoethanol (3.75 g), 1-(4-piperidinyl)-1H-indole (5 g) and sodium hydrogen carbonate (4.2 g) in ethanol (100 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was stirred in water and this mixture was extracted with CH2Cl2. The separated organic layer was dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE and the solvent was evaporated, yielding 4 g (64%) of 4-(1H-indol-1-yl)-1-piperidineethanol (intermediate 8).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. stirringThe residue was stirred in water
  4. extractionthis mixture was extracted with CH2Cl2
  5. dry with materialThe separated organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. stirringThe residue was stirred in DIPE
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fe4e4315e4ad44858b4b7ae5bc44681b
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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