Hydrochloric Acid → HCID 12298140, compound

HRID 1973811Notes

Reaction equation

HRID 1973811 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:22](N)=[O:23])[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[OH-:25].[K+].Cl.[OH-].[Na+]>O.C(O)CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:22]([OH:25])=[O:23])[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 708841-Benzyl-4-(p-toluidino)piperidine-4-carboxamide

Product 1

HCID 12298140HCID 12298140, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

A mixture of 100 parts of 4-[(4-methylphenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxamide, 52.2 parts of potassium hydroxide and 638 parts of 1,2-ethanediol is stirred and refluxed for 25 hours. After cooling, 1200 parts of water are added and the whole is acidified with a concentrated hydrochloric acid solution. The acid aqueous phase is alkalized with a sodium hydroxide solution 60%: exothermic reaction. After cooling, the precipitated crude product is filtered off and dissolved in water. This solution is acidified with acetic acid (pH about 6.5) and the product is filtered off. It is crystallized from N,N-dimethylformamide, filtered off again, washed with 2-propanone and dried, yielding 4-[(4-methylphenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxylic acid; mp. 270° C.

Workup

  1. temperaturerefluxed for 25 hours
  2. temperatureAfter cooling
  3. customexothermic reaction
  4. temperatureAfter cooling
  5. customthe precipitated crude product
  6. filtrationis filtered off
  7. dissolutiondissolved in water
  8. filtrationthe product is filtered off
  9. customIt is crystallized from N,N-dimethylformamide
  10. filtrationfiltered off again
  11. washwashed with 2-propanone
  12. customdried

Sources & evidence

ORD record
ord-5a2f120e81b748f29d12e5e3518eaf86
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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