Ethylene Glycol → HCID 20382290, compound

HRID 1448330Notes

Reaction equation

HRID 1448330 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:23]([O:25]CC)=[O:24])[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[OH-].[K+].C(O)CO>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:23]([OH:25])=[O:24])[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 20382197HCID 20382197, compound

Product 1

HCID 20382290HCID 20382290, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 60.1 parts of ethyl 4-[(4-methylphenyl)amino]-1-(2-phenylethyl)-4-piperidinecarboxylate, 27.6 parts of potassium hydroxide and 150 parts of 1,2-ethanediol is stirred and refluxed for 3 hours. The reaction mixture is cooled to room temperature and poured onto water. The whole is neutralized with acetic acid. The precipitated product is filtered off and crystallized from N,N-dimethylformamide. The product is filtered off and dried in vacuo, yielding 43.9 parts (79.2%) of 4-[(4-methylphenyl)amino]-1-(2-phenylethyl)-4-piperidinecarboxylic acid; mp. 264.6° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. additionpoured onto water
  3. filtrationThe precipitated product is filtered off
  4. customcrystallized from N,N-dimethylformamide
  5. filtrationThe product is filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2fad9b62c42341dc8e8a76bc83d87547
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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