Ethanol → 2-[4-(4-Methylbenzyl)-piperidino]-4'-hydroxypropiophenone

HRID 2308749Notes

Reaction equation

HRID 2308749 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(O)C.Br[CH:19]([CH3:29])[C:20]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH:19]([CH3:29])[C:20]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)=[O:21])[CH2:9][CH2:8]2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 33756034-[(4-Methylphenyl)methyl]piperidineHCID 126131632-Bromo-1-(4-hydroxyphenyl)propan-1-one

Product 1

HCID 133224472-[4-(4-Methylbenzyl)-piperidino]-4'-hydroxypropiophenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

7.57 g (0.04 mol) of 4-(4-methylbenzyl)-piperidine are introduced into 35 ml of ethanol, 9.15 g (0.04 mol) of 2-bromo-4'-hydroxypropiophenone and then 4.24 g (0.04 mol) of sodium carbonate are added and the mixture is heated under reflux for 2 hours. It is then cooled with an ice bath and 200 ml of iced water and 100 ml of toluene are added. The mixture is stirred and left to separate and the organic phase is separated off. The aqueous phase is extracted three times with 100 ml of toluene. The organic phases are combined, washed, dried and then evaporated. This gives 13 g of a pasty oil, which is purified by chromatography on silica using acetone as the eluant. 10 g of a pale oil are collected, which is used as such in the subsequent reduction.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. temperatureIt is then cooled with an ice bath
  4. waitleft
  5. customto separate
  6. customthe organic phase is separated off
  7. extractionThe aqueous phase is extracted three times with 100 ml of toluene
  8. washwashed
  9. customdried
  10. customevaporated
  11. customThis gives 13 g of a pasty oil, which is purified by chromatography on silica
  12. custom10 g of a pale oil are collected

Sources & evidence

ORD record
ord-c798c94c635c4a56a29b9cb7d35d439b
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

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