Potassium Carbonate → 2-(4-Benzylpiperidino)-4'-ethylpropiophenone

HRID 2308760Notes

Reaction equation

HRID 2308760 reaction equation
Br[CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].[CH2:14]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:14]([CH:21]1[CH2:26][CH2:25][N:24]([CH:2]([CH3:13])[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][CH:6]=2)=[O:4])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 201874952-Bromo-4'-ethylpropiophenone

Product 1

HCID 201874892-(4-Benzylpiperidino)-4'-ethylpropiophenone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 17.2 g of 2-bromo-4'-ethylpropiophenone, 12.5 g of 4-benzylpiperidine and 9.9 g of potassium carbonate in 250 ml of dry ethanol is heated under reflux for 4 hours, with stirring. The inorganic product is filtered off and washed with ethanol and the alcohol phase is concentrated in vacuo. The oily residue is taken up in diethyl ether and the mixture is extracted twice with dilute hydrochloric acid. After it has been rendered clearly alkaline with sodium hydroxide, the acid aqueous phase is then extracted three times with ethyl acetate. The organic phases are combined, washed with water until the washings are neutral, dried and evaporated in vauco. This give 19.15 g of an oily residue.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe inorganic product is filtered off
  4. washwashed with ethanol
  5. concentrationthe alcohol phase is concentrated in vacuo
  6. extractionthe mixture is extracted twice with dilute hydrochloric acid
  7. extractionthe acid aqueous phase is then extracted three times with ethyl acetate
  8. washwashed with water until the washings
  9. customdried
  10. customevaporated in vauco

Sources & evidence

ORD record
ord-28e10ce533724c5f8a8e2e720c0f0f9b
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

Loading…