Potassium Carbonate → HCID 20544142, compound

HRID 2285781Notes

Reaction equation

HRID 2285781 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][N:6]([CH3:8])[C:5](=[O:9])[C:4]1([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.[C:36](=[O:39])([O-:38])[O-].[K+].[K+]>C(O)C>[C:5]([OH:35])(=[O:9])/[CH:4]=[CH:16]/[C:36]([OH:38])=[O:39].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2([OH:35])[CH2:30][CH2:31][N:32]([CH2:2][CH:3]3[CH2:7][N:6]([CH3:8])[C:5](=[O:9])[C:4]3([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:33][CH2:34]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 12822292HCID 12822292, compound

Product 1

HCID 20544142HCID 20544142, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

To a steel bomb was added 17.0 g. (0.057 mole) of 4-chloromethyl-1-methyl-3,3-diphenyl-2-pyrrolidinone in 150 ml. of ethanol, 12.0 g. (0.057 mole) of 4-(p-chlorophenyl)-4-hydroxypiperidine and 21.2 g. (0.17 mole) of finely ground potassium carbonate. The mixture was heated with stirring to 200° C. for 48 hours. After concentrating the mixture in vacuo, the residue was partitioned between dilute hydrochloric acid solution and isopropyl ether. The ether was discarded, the acid solution was made basic with 50 percent sodium hydroxide solution and the base insoluble material was extracted with chloroform. The chloroform was dried, filtered and concentrated in vacuo. The residue was dissolved in a mixture of isopropyl ether and isopropanol and treated with an equivalent of fumaric acid. The fumarate salt was recrystallized twice from ethanol and once from isopropanol-methanol. The fumarate salt (2.0 g., 10%) melted at 213°-215° C.

Workup

  1. temperatureThe mixture was heated
  2. concentrationAfter concentrating the mixture in vacuo
  3. customthe residue was partitioned between dilute hydrochloric acid solution and isopropyl ether
  4. extractionthe base insoluble material was extracted with chloroform
  5. dry with materialThe chloroform was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in a mixture of isopropyl ether and isopropanol
  9. additiontreated with an equivalent of fumaric acid
  10. customThe fumarate salt was recrystallized twice from ethanol and once from isopropanol-methanol

Sources & evidence

ORD record
ord-7e21f31511074d3fa6260799809ac274
Source dataset
uspto-grants-1982_04
Patent number
US04324791

Reaction notes

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