Potassium Carbonate → HCID 12822302, compound

HRID 1112286Notes

Reaction equation

HRID 1112286 reaction equation
[CH:1]1([N:7]2[CH2:11][CH:10]([CH2:12]Cl)[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[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)([O-])[O-].[K+].[K+]>C(O)C>[CH:1]1([N:7]2[CH2:11][CH:10]([CH2:12][N:31]3[CH2:32][CH2:33][C:28]([OH:27])([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH2:29][CH2:30]3)[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 128222931-Cyclohexyl-4-chloromethyl-3,3-diphenyl-2-pyrrolidinone

Product 1

HCID 12822302HCID 12822302, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

To 150 ml. of ethanol in a steel bomb was added 15.0 g. (0.041 mole) of 1-cyclohexyl-4-chloromethyl-3,3-diphenyl-2-pyrrolidinone, 7.23 g. (0.041 mole) of 4-hydroxy-4-phenyl piperidine and 17.0 g. (0.12 mole) of potassium carbonate. The bomb was heated in an oven at 200° C. with stirring for 48 hours. The mixture was concentrated in vacuo, and the residue was partitioned between dilute sodium hydroxide solution and chloroform. The chloroform layer was dried, filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate and treated with ethereal hydrogen chloride. The solid which precipitated was the hydrochloride of starting piperidine compound. A further precipitate from the filtrate of this material contained a by-product of the reaction. The by-product was separated by filtration and the filtrate concentrated. The residue was partitioned between chloroform and sodium hydroxide solution, and the chloroform, after drying, was concentrated in vacuo. The residue was placed on a magnesium silicate column using chloroform as the eluent. The product was obtained upon subsequent washings of 1 and 2 percent methanol in chloroform. The washings were concentrated in vacuo, and the residue crystallized using an isopropyl ether-ethyl acetate mixture. The solid (1.5 g.; m.p. 179°-184° C.) after recrystallizing from ethyl acetate weighed 1.0 g. and melted at 188°-190° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between dilute sodium hydroxide solution and chloroform
  3. dry with materialThe chloroform layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. additiontreated with ethereal hydrogen chloride
  8. customThe solid which precipitated
  9. customa by-product of the reaction
  10. customThe by-product was separated by filtration
  11. concentrationthe filtrate concentrated
  12. customThe residue was partitioned between chloroform and sodium hydroxide solution
  13. dry with materialthe chloroform, after drying
  14. concentrationwas concentrated in vacuo
  15. customThe product was obtained upon subsequent washings of 1 and 2 percent methanol in chloroform
  16. concentrationThe washings were concentrated in vacuo
  17. customthe residue crystallized
  18. customThe solid (1.5 g.; m.p. 179°-184° C.) after recrystallizing from ethyl acetate

Sources & evidence

ORD record
ord-fcebc09ac7934226b638abf0c16f8edc
Source dataset
uspto-grants-1978_10
Patent number
US04120969

Reaction notes

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