Potassium Carbonate → HCID 20187500, compound

HRID 2308751Notes

Reaction equation

HRID 2308751 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([CH3:18])[C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:10].[CH3:19][O:20][C:21]1[CH:33]=[CH:32][C:24]([CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:23][CH:22]=1>C(O)C>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([CH:8]([CH3:18])[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[O:10])[CH2:30][CH2:31]2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 37327404-((4-Methoxyphenyl)methyl)piperidineHCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-one

Product 1

HCID 20187500HCID 20187500, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.80 g (0.02 mol) of potassium carbonate are added to a solution of 5 g (0.02 mol) of 2-bromo-4'-chloropropiophenone and 4.15 g (0.02 mol) of 4-(4-methoxybenzyl)-piperidine in 60 ml of dry ethanol and the mixture is heated under reflux for 5 hours, with stirring, and then left to stand for 48 hours. It is left to cool and filtered, the filter cake being washed with alcohol, and the filtrate is evaporated. An orange oily residue remains, which is taken up in a mixture of water and diethyl ether. The organic phase is separated off and the aqueous phase is extracted a second time with diethyl ether. The organic phases are combined, dried and evaporated to give 7.45 g of an orange-yellow oily residue, which crystallises partially at ambient temperature and which is used as such in the subsequent reduction.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 hours
  3. waitleft
  4. waitIt is left
  5. temperatureto cool
  6. filtrationfiltered
  7. washthe filter cake being washed with alcohol
  8. customthe filtrate is evaporated
  9. additionwhich is taken up in a mixture of water and diethyl ether
  10. customThe organic phase is separated off
  11. extractionthe aqueous phase is extracted a second time with diethyl ether
  12. customdried
  13. customevaporated

Sources & evidence

ORD record
ord-69440df4d99342908afc1132fcf767d4
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

Loading…