Potassium Carbonate → HCID 15463127, compound

HRID 613258Notes

Reaction equation

HRID 613258 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][CH:14]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24](Cl)=[CH:23][CH:22]=1)[CH2:15][C:16]([OH:18])=[O:17].C(=O)([O-])[O-:29].[K+].[K+]>CS(C)=O.O>[CH3:13][CH:14]([CH2:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)=[CH:23][CH:22]=1)[CH2:15][C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 19592186HCID 19592186, compound

Product 1

HCID 15463127HCID 15463127, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A stirred mixture of 4-phenylpiperidine (0.161 g, 1.00 mmol), (±)3-methyl-5-(4-chloro-phenyl)-pentanoic acid (0.241 g, 1.00 mol), and potassium carbonate (0.276 g, 2.00 mol) in dry dimethyl sulfoxide was heated in a sand bath (160° C.) under nitrogen for 15 hours. The mixture was cooled and diluted with water. The aqueous solution was filtered, and the filtrate was acidified with concentrated hydrochloric acid to pH=6. A brown gum formed. The liquid was decanted, and the residue was chromatographed on silica gel (38 g, 230-400 mesh) eluting with dichloromethane-methanol (20:1, 15×40 mL). Fractions containing product were combined and rotary evaporated to give a brown glass. The glass was crystallized from methanol after a hot gravity filtration to give the title compound as a tan solid; yield 0.0360 g (10%, mp=134-135° C.).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe aqueous solution was filtered
  3. customA brown gum formed
  4. customThe liquid was decanted
  5. customthe residue was chromatographed on silica gel (38 g, 230-400 mesh)
  6. washeluting with dichloromethane-methanol (20:1, 15×40 mL)
  7. additionFractions containing product
  8. customrotary evaporated
  9. customto give a brown glass
  10. customThe glass was crystallized from methanol
  11. filtrationafter a hot gravity filtration

Sources & evidence

ORD record
ord-18fa6cd47a904585b47dc031b0a86665
Source dataset
uspto-grants-1999_12
Patent number
US06008220

Reaction notes

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