Potassium Carbonate → HCID 20187496, compound

HRID 2308766Notes

Reaction equation

HRID 2308766 reaction equation
Br[CH:2]([CH3:16])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)=[O:4].[CH2:17]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:17]([CH:24]1[CH2:29][CH2:28][N:27]([CH:2]([CH3:16])[C:3]([C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=2)=[O:4])[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 13322442HCID 13322442, compound

Product 1

HCID 20187496HCID 20187496, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

300 ml of methyl ethyl ketone containing 57.4 g of 2-bromo-4'-hydroxy-3'-methoxycarbonylpropiophenone, 35 g of 4-benzylpiperidine and 30.6 g of potassium carbonate are heated under reflux for 4 hours. The precipitate is filtered off hot, the filtrate is evaporated to dryness, the residue is taken up in 3N hydrochloric acid and the mixture is extracted with diethyl ether. The ether phase is stirred for one hour; the hydrochloride crystallizes and is filtered off, rinsed with diethyl ether and transferred to a beaker containing water rendered alkaline with 3N aqueous ammonia solution, and the base freed in this way is extracted with ethyl acetate. After washing, drying and evaporation of the organic phase, 52 g of product are obtained, which is used as such.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationThe precipitate is filtered off hot
  3. customthe filtrate is evaporated to dryness
  4. extractionthe mixture is extracted with diethyl ether
  5. customthe hydrochloride crystallizes
  6. filtrationis filtered off
  7. washrinsed with diethyl ether
  8. additioncontaining water rendered alkaline with 3N aqueous ammonia solution
  9. extractionis extracted with ethyl acetate
  10. washAfter washing
  11. customdrying
  12. customevaporation of the organic phase, 52 g of product
  13. customare obtained

Sources & evidence

ORD record
ord-3594a436ec4d4e778e5716afb8c20910
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

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