Potassium Carbonate → HCID 23036293, compound

HRID 1193708Notes

Reaction equation

HRID 1193708 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][CH2:29][CH2:30]Br)=[C:25]([O:34][CH3:35])[CH:24]=1)(=[O:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].O.O.[C:44]([OH:49])(=[O:48])[C:45]([OH:47])=[O:46]>CCOCC.C1(C)C=CC=CC=1>[OH2:22].[C:44]([OH:49])(=[O:48])[C:45]([OH:47])=[O:46].[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:9][CH2:10][N:11]([CH2:30][CH2:29][CH2:28][O:27][C:26]3[CH:32]=[CH:33][C:23]([C:20](=[O:22])[CH3:21])=[CH:24][C:25]=3[O:34][CH3:35])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 61373Oxalic acid dihydrateHCID 27625334-(Diphenylmethylene)piperidineHCID 184039631-[4-(3-Bromopropoxy)-3-methoxyphenyl]ethan-1-one

Product 1

HCID 23036293HCID 23036293, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.5 g (0.03 mole) of 4-diphenylmethylenepiperidine, 6.3 g (0.032 mole) of 3-(p-acetyl-o-methoxyphenoxy)propyl bromide, 25 g of potassium carbonate and 150 ml of toluene was heated at reflux for 16 hrs, cooled, filtered and the solvent evaporated at reduced pressure. The residual oil was taken up in benzene, washed with water, dried over magnisium sulfate and then the solvent was evaporated. The free base was dissolved in isopropanol and treated with 3.8 g (0.03 mole) of oxalic acid dihydrate in dry ether. The white salt which separated was recrystallized from an isopropanol-methanol mixture. The product weighed 8.5 g(54%). m.p. 186°-188° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hrs
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe solvent evaporated at reduced pressure
  6. washwashed with water
  7. dry with materialdried over magnisium sulfate
  8. customthe solvent was evaporated
  9. dissolutionThe free base was dissolved in isopropanol
  10. customThe white salt which separated
  11. customwas recrystallized from an isopropanol-methanol mixture

Sources & evidence

ORD record
ord-d8678c43398f426f8493b97ce4ba9b69
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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