Hydrochloric Acid → HCID 12298142, compound

HRID 1973813Notes

Reaction equation

HRID 1973813 reaction equation
Cl.[C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][C:12]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)([C:15](N)=[O:16])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:29].[Na+]>O>[C:2]1([CH2:8][N:9]2[CH2:10][CH2:11][C:12]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)([C:15]([OH:16])=[O:29])[CH2:13][CH2:14]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12298135HCID 12298135, compound

Product 1

HCID 12298142HCID 12298142, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 792 parts of concentrated hydrochloric acid solution are added 100 parts of 1-(phenylmethyl)-4-{[3-(trifluoromethyl)phenyl]amino}-4-piperidinecarboxamide. The whole is heated to reflux temperature while stirring. 230 Parts of water are added followed by the addition of anti-foam. Stirring at reflux is continued for 3.50 h. After cooling to room temperature, the reaction mixture is poured into a vessel and 200 parts of water are added. The whole is strongly alkalized with sodium hydroxide while stirring vigorously: a precipitate is formed. The supernatant aqueous phase is decanted and the residual precipitate is dissolved in water. The resulting solution is cooled and acidified with acetic acid (pH = about 7), whereupon the product is precipitated. It is filtered off and boiled in N,N-dimethylformamide. After cooling, the product is filtered off again, washed successively with ethanol and 2,2'-oxybispropane and dried. The less pure fraction is crystallized from N,N-dimethylformamide. The pure product is filtered off, washed successively with ethanol and with N,N-dimethylformamide, and dried at 140° C, yielding 1-(phenylmethyl)-4-[ 3-(trifluoromethyl)phenylamino]-4-piperidinecarboxylic acid; mp. 264.3° C.

Workup

  1. temperatureThe whole is heated
  2. temperatureto reflux temperature
  3. additionfollowed by the addition of anti-foam
  4. stirringStirring
  5. temperatureat reflux
  6. additionthe reaction mixture is poured into a vessel
  7. stirringwhile stirring vigorously
  8. customa precipitate is formed
  9. customThe supernatant aqueous phase is decanted
  10. dissolutionthe residual precipitate is dissolved in water
  11. temperatureThe resulting solution is cooled
  12. customis precipitated
  13. filtrationIt is filtered off
  14. temperatureAfter cooling
  15. filtrationthe product is filtered off again
  16. washwashed successively with ethanol and 2,2'-oxybispropane
  17. customdried
  18. customThe less pure fraction is crystallized from N,N-dimethylformamide
  19. filtrationThe pure product is filtered off
  20. washwashed successively with ethanol and with N,N-dimethylformamide
  21. customdried at 140° C

Sources & evidence

ORD record
ord-c06eb941fc76455ca2959991b549da9d
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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