4-Phenylpiperidin-4-ol → HCID 22629575, compound

HRID 276908Notes

Reaction equation

HRID 276908 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[N:8]([CH3:18])[C:7]2=[O:19].[OH:20][C:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)(O)[O-].[Na+]>C(O)C>[OH:20][C:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]23[CH2:17][CH2:16][CH2:15][C:13]4[C:14]2=[C:9]([CH:10]=[CH:11][CH:12]=4)[N:8]([CH3:18])[C:7]3=[O:19])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 963874-Phenylpiperidin-4-olHCID 516892Sodium BicarbonateHCID 110563612a-(4-Bromobutyl)-1-methyl-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

Product 1

HCID 22629575HCID 22629575, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2a-(4-bromobutyl)-1-methyl-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (322 mg, 1 mmol), 4-hydroxy-4-phenylpiperidine (210 mg, 1.2 mmol), sodium bicarbonate (102 mg, 1.2 mmol) and ethanol (15 ml) was heated under reflux for 6.3 hours on an oil bath, the reaction solution was cooled, and the thus precipitated crystals were collected by filtration to obtain 226 mg of the title compound (0.54 mmol, 54% in yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6.3 hours on an oil bath
  3. temperaturethe reaction solution was cooled
  4. filtrationthe thus precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-d1487146c1964acb8e6aedcf6a00df6c
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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