Potassium Carbonate → HCID 20544126, compound

HRID 1112288Notes

Reaction equation

HRID 1112288 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][N:6]([CH:8]([CH3:10])[CH3:9])[C:5](=[O:11])[C:4]1([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2([OH:37])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1.[C:38](=[O:41])([O-:40])[O-].[K+].[K+]>C(O)C>[OH2:11].[C:5]([OH:11])(=[O:37])[C:38]([OH:40])=[O:41].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2([OH:37])[CH2:32][CH2:33][N:34]([CH2:2][CH:3]3[CH2:7][N:6]([CH:8]([CH3:9])[CH3:10])[C:5](=[O:11])[C:4]3([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:35][CH2:36]2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 12953546HCID 12953546, compound

Product 1

HCID 20544126HCID 20544126, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 18 g. (0.06 mole) of 4-chloromethyl-1-(1-methylethyl)-3,3-diphenyl-2-pyrrolidinone, 11.6 g. (0.06 mole) of 4-(4-chlorophenyl)-4-hydroxypiperidine and 20 g. (0.14 mole) potassium carbonate in 200 ml. of ethanol was heated to 200° C. for 48 hrs. in a steel bomb. During the heating the bomb was continuously rotated to produce mild stirring. The mixture was concentrated and the residue partitioned between chloroform sodium hydroxide. The chloroform was dried (sodium sulfate) and concentrated. The residue was dissolved in ethyl-acetate and treated with ethereal hydrogen chloride. The mixture was filtered and the filtrate extracted with water. The acid layer was made basic with dilute sodium hydroxide and extracted with chloroform which was dried (sodium sulfate) and concentrated. The residue was dissolved in isopropyl alcohol and treated with oxalic acid. The resulting crystals were recrystallized from ethanol-water. The product (3 g., 10%) melted at 240° C. (dec.).

Workup

  1. additionA mixture of 18 g
  2. customto produce mild stirring
  3. concentrationThe mixture was concentrated
  4. customthe residue partitioned between chloroform sodium hydroxide
  5. dry with materialThe chloroform was dried (sodium sulfate)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ethyl-acetate
  8. additiontreated with ethereal hydrogen chloride
  9. filtrationThe mixture was filtered
  10. extractionthe filtrate extracted with water
  11. extractionextracted with chloroform which
  12. dry with materialwas dried (sodium sulfate)
  13. concentrationconcentrated
  14. dissolutionThe residue was dissolved in isopropyl alcohol
  15. additiontreated with oxalic acid
  16. customThe resulting crystals were recrystallized from ethanol-water

Sources & evidence

ORD record
ord-5be9cc830539479fa034c59b60f61fd4
Source dataset
uspto-grants-1978_10
Patent number
US04120969

Reaction notes

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