Potassium Carbonate → HCID 23036293, compound

HRID 1709892Notes

Reaction equation

HRID 1709892 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 (0.030 mole) of 4-diphenylmethylenepiperidine, 6.3 g (0.032 mole) of 3-(p-acetyl-o-methoxyphenoxy)propyl bromide, 25 g (0.18 mole) of potassium carbonate and 150 ml of toluene was heated at reflux for 16 hr, cooled, filtered and the solvent evaporated at reduced pressure. The residual oil was dissolved in benzene, washed with water, dried over magnesium sulfate and then the solvent was evaporated. The free base was dissolved in 2-propanol and treated with 3.8 g (0.03 mole) of oxalic acid dihydrate in dry ether. The white salt which separated was recrystallized from a 2-propanol-methanol mixture. The produce weighed 8.5 g (54%), m.p. 186°-188° C.

Workup

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

Sources & evidence

ORD record
ord-741efa3feda24919aee3805b7ebce25a
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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