Potassium Carbonate → Oxalate

HRID 2285780Notes

Reaction equation

HRID 2285780 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.[OH:22][C:23]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[C:35](=[O:38])([O-:37])[O-].[K+].[K+]>C(O)C>[C:5]([OH:22])(=[O:9])/[CH:4]=[CH:16]/[C:35]([OH:37])=[O:38].[CH3:8][N:6]1[CH2:7][CH:3]([CH2:2][N:26]2[CH2:27][CH2:28][C:23]([OH:22])([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:25]2)[C:4]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]1=[O:9].[C:5]([O-:9])(=[O:22])[C:35]([O-:37])=[O:38]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 12822292HCID 12822292, compound

Product 2

HCID 71081OxalateHCID 20544123HCID 20544123, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

To 100 ml. of ethanol was added 10.0 g. (0.033 mole) of 4-chloromethyl-1-methyl-3,3-diphenyl-2-pyrrolidinone, 5.8 g. (0.033 mole) of 4-hydroxy-4-phenylpiperidine and 13.8 g. (0.10 mole) of potassium carbonate (finely ground). The mixture was heated in a steel bomb with stirring in an oven for 48 hours at 200° C. After concentrating in vacuo, the residue was partitioned between dilute sodium hydroxide solution and chloroform. The chloroform was dried, filtered and concentrated in vacuo. The residue was dissolved in isopropanol and treated with oxalic acid, and the starting piperidine compound was obtained as an oxalate. The filtrate was concentrated in vacuo, and the residue was partitioned between dilute hydrochloric acid and ethyl acetate. The acid solution was made basic with dilute sodium hydroxide and was extracted with chloroform. The chloroform solution was dried (sodium sulfate), filtered and concentrated in vacuo. The residue was dissolved in hot isopropyl ether and treated with an equivalent amount of fumaric acid dissolved in isopropanol. The resulting salt was recrystallized from ethanol. The salt was triturated with acetonitrile to remove ethanol in the form of a solvate and dried. The salt (2.5 g., 14%) melted at 202°-205° C.

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe residue was partitioned between dilute sodium hydroxide solution and chloroform
  3. dry with materialThe chloroform was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in isopropanol
  7. additiontreated with oxalic acid

Sources & evidence

ORD record
ord-70f08ad35b0e4dc0be6f4e5597c69d02
Source dataset
uspto-grants-1982_04
Patent number
US04324791

Reaction notes

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