trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamide → trans-N-(3-methoxy-4-piperidinyl)-3-(trifluoromethyl)benzamide

HRID 981302Notes

Reaction equation

HRID 981302 reaction equation
[CH3:1][O:2][C@H:3]1[C@H:8]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH2:7][CH2:6][N:5](CC2C=CC=CC=2)[CH2:4]1.[H][H]>[Pd].CO>[CH3:1][O:2][C@H:3]1[C@H:8]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[CH2:7][CH2:6][NH:5][CH2:4]1

Participants

5

Reactant 2

HCID 67928762trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 67928786trans-N-(3-methoxy-4-piperidinyl)-3-(trifluoromethyl)benzamideYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 12 parts of trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamide and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was solidified on scratching in 2,2'-oxybispropane. The precipitated product was filtered off and dissolved in 135 parts of methylbenzene and 105 parts of 1,1'-oxybisethane. The supernatant liquid was decanted, washed twice with a dilute ammonium hydroxide solution and the product was extracted with methylbenzene. The aqueous phase was saturated with potassium carbonate and the product was extracted with methylbenzene. The combined organic layers were dried, filtered and evaporated in vacuo, yielding 6.43 parts (71%) of trans-N-(3-methoxy-4-piperidinyl)-3-(trifluoromethyl)benzamide; mp. 100.3° C. (interm. 9).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. filtrationThe precipitated product was filtered off
  4. dissolutiondissolved in 135 parts of methylbenzene and 105 parts of 1,1'-oxybisethane
  5. customThe supernatant liquid was decanted
  6. washwashed twice with a dilute ammonium hydroxide solution
  7. extractionthe product was extracted with methylbenzene
  8. extractionthe product was extracted with methylbenzene
  9. customThe combined organic layers were dried
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-d5a116b674464030a04cb9d0e77792c4
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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