Hydrochloric Acid → 4-[(3-Methoxyphenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxylic acid

HRID 1973803Notes

Reaction equation

HRID 1973803 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2([C:23](N)=[O:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1.[OH-:26].[K+].Cl.[OH-].[Na+]>O.C(O)CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2([C:23]([OH:26])=[O:24])[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 12298120HCID 12298120, compound

Product 1

HCID 122981384-[(3-Methoxyphenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

A mixture of 100 parts of 4-[N-(3-methoxyphenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxamide, 49.5 parts of potassium hydroxide and 974 parts of 1,2-ethanediol is stirred and refluxed for 24 hours. After cooling, the reaction mixture is poured onto 1500 parts of water and acidified with a concentrated hydrochloric acid solution. The whole is strongly alkalized with a sodium hydroxide solution and the layers are separated. The aqueous phase is concentrated, whereupon the product is separated as an oil. The supernatant aqueous phase is decanted and the residual oil is taken up in a sodium hydroxide solution. The precipitated product is filtered off and dissolved in water. The solution is acidified with acetic acid till pH = 6. The precipitated product is filtered off and warmed in ethanol. It is filtered off again, washed with ethanol and 2,2'-oxybispropane and dissolved in boiling N,N-dimethylformamide. The solution is filtered and the product is allowed to crystallized from the filtrate. It is filtered off, washed successively with N,N-dimethylformamide, water and ethanol, and dried, yielding 4-[N-(3-methoxyphenyl)amino]- 1-(phenylmethyl)-4-piperidinecarboxylic acid; mp. 211.1° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureAfter cooling
  3. customthe layers are separated
  4. concentrationThe aqueous phase is concentrated, whereupon the product
  5. customis separated as an oil
  6. customThe supernatant aqueous phase is decanted
  7. filtrationThe precipitated product is filtered off
  8. dissolutiondissolved in water
  9. filtrationThe precipitated product is filtered off
  10. temperaturewarmed in ethanol
  11. filtrationIt is filtered off again
  12. washwashed with ethanol and 2,2'-oxybispropane
  13. dissolutiondissolved
  14. filtrationThe solution is filtered
  15. customto crystallized from the filtrate
  16. filtrationIt is filtered off
  17. washwashed successively with N,N-dimethylformamide, water and ethanol
  18. customdried

Sources & evidence

ORD record
ord-2eeea6b75e8f4b9f894cba3f3bfd0535
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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