Potassium Carbonate → HCID 20544160, compound

HRID 2285783Notes

Reaction equation

HRID 2285783 reaction equation
[Cl:1][CH2:2][CH:3]1[CH2:7][NH:6][C:5](=[O:8])[C:4]1([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[OH:27][C:28]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(O)C>[ClH:1].[OH:27][C:28]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:33][CH2:32][N:31]([CH2:2][CH:3]2[CH2:7][NH:6][C:5](=[O:8])[C:4]2([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 12822295HCID 12822295, compound

Product 1

HCID 20544160HCID 20544160, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

To 10.0 g. (0.035 mole) of 4-(chloromethyl)-3,3-diphenyl-2-pyrrolidinone in 150 ml. of ethanol in a steel bomb was added 15.0 g. (0.11 mole) of potassium carbonate (finely ground) and 6.2 g. (0.035 mole) of 4-hydroxyl-4-phenylpiperidine. The mixture was heated to 200° C. for 48 hours and rotated slowly to effect mild stirring. After concentrating in vacuo, the residue was partitioned between dilute hydrochloric acid solution and ethyl acetate. The acid solution was made basic with sodium hydroxide and extracted with chloroform. The chloroform was dried, filtered and concentrated in vacuo. The residue was dissolved in isopropanol and treated with oxalic acid, and the oxalate salt of the starting piperidine compound precipitated out. The filtrate was concentrated in vacuo and the residue was partitioned between dilute sodium hydroxide and chloroform. The chloroform solution was dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate and a solid formed which was filtered off. The filtrate was treated with ethereal hydrogen chloride and the hydrochloride salt was recrystallized in isopropanol-methanol. The salt (2.6 g., 17%) melted above 250° C.

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe residue was partitioned between dilute hydrochloric acid solution and ethyl acetate
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in isopropanol
  8. additiontreated with oxalic acid
  9. customthe oxalate salt of the starting piperidine compound precipitated out
  10. concentrationThe filtrate was concentrated in vacuo
  11. customthe residue was partitioned between dilute sodium hydroxide and chloroform
  12. dry with materialThe chloroform solution was dried (sodium sulfate)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. dissolutionThe residue was dissolved in ethyl acetate
  16. customa solid formed which
  17. filtrationwas filtered off
  18. additionThe filtrate was treated with ethereal hydrogen chloride
  19. customthe hydrochloride salt was recrystallized in isopropanol-methanol
  20. custommelted above 250° C.

Sources & evidence

ORD record
ord-bad807f8250446bcbe64ddb963a08187
Source dataset
uspto-grants-1982_04
Patent number
US04324791

Reaction notes

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