HCID 86756201, compound → HCID 70221472, compound

HRID 564888Notes

Reaction equation

HRID 564888 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:37]=[C:38]([CH3:40])[CH:39]=1)[C:5]([N:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:18][CH2:17][C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:19]([O:21]CC)=[O:20])[CH2:15][CH2:14]2)[CH2:9][C@@H:8]1[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:6]>[OH-].[Na+].O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:37]=[C:38]([CH3:40])[CH:39]=1)[C:5]([N:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:18][CH2:17][C:16]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]2)[CH2:9][C@@H:8]1[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:6]

Participants

4

Reactant 1

HCID 86756201HCID 86756201, compound

Product 1

HCID 70221472HCID 70221472, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (±)-ethyl cis-1-[1-(3,5dimethylbenzoyl)-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinecarboxylate (2.96 g) in NaOH (20 ml) and dioxane (50 ml) was stirred and refluxed for 30 hours. The mixture was evaporated and HCl, (1N; 20 ml) was added. The precipitate was filtered off, water (100 ml) and CH2Cl2 (10 ml) were added and filtered again. The precipitate was taken up in water, heated, cooled, filtered off and dried. The product was purified by HPLC (eluent: ammoniumacetate and CH3CN). The pure fractions were collected, evaporated and dried, yielding 1.09 g (39%) of (±)-cis-1-[1-(3,5-dimethylbenzoyl)-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinecarboxylic acid (compound 38, mp. 259.1° C.).

Workup

  1. temperaturerefluxed for 30 hours
  2. customThe mixture was evaporated
  3. additionHCl, (1N; 20 ml) was added
  4. filtrationThe precipitate was filtered off
  5. additionwater (100 ml) and CH2Cl2 (10 ml) were added
  6. filtrationfiltered again
  7. temperatureheated
  8. temperaturecooled
  9. filtrationfiltered off
  10. customdried
  11. customThe product was purified by HPLC (eluent: ammoniumacetate and CH3CN)
  12. customThe pure fractions were collected
  13. customevaporated
  14. customdried

Sources & evidence

ORD record
ord-2fdbdff377d24685bab15c8e6821a261
Source dataset
uspto-grants-2001_01
Patent number
US06169097A

Reaction notes

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