Hydrochloric Acid → HCID 20382243, compound

HRID 1448334Notes

Reaction equation

HRID 1448334 reaction equation
C(O)(=O)C(O)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2([C:30]([O:32]C)=[O:31])[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][CH2:17]2)[CH:12]=[CH:13][CH:14]=1.[OH-].[K+].Cl.[OH-].[Na+]>O.C(O)CO>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2([C:30]([OH:32])=[O:31])[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:20][CH2:21]2)[CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 12298196HCID 12298196, compound

Product 1

HCID 20382243HCID 20382243, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

A mixture of 39.5 parts of methyl 4-[N-(3-methoxyphenyl)amino]-1-(2-phenylethyl)-4-piperidinecarboxylate ethanedioate, 18 parts of potassium hydroxide and 90 parts of 1,2-ethanediol is stirred and refluxed for 3 hours. The reaction mixture is cooled to room temperature, poured onto 200 parts of water and acidified with a concentrated hydrochloric acid solution. The whole is strongly alkalized with a sodium hydroxide solution and stirred vigorously for one hour. The precipitated product is filtered off, dissolved in water and the solution is neutralized with acetic acid. The product is filtered off and crystallized from N,N-dimethylformamide, yielding 27.4 parts (72.3%) of 4-[(3-methoxyphenyl)amino]-1-(2-phenylethyl)-4-piperidinecarboxylic acid; mp. 265.1° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. stirringstirred vigorously for one hour
  3. filtrationThe precipitated product is filtered off
  4. dissolutiondissolved in water
  5. filtrationThe product is filtered off
  6. customcrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-dd6228f6d473424a885b267af8e70d5c
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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