Potassium Hydroxide → HCID 23339051, compound

HRID 236753Notes

Reaction equation

HRID 236753 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH:22]2[CH2:27][CH2:26][N:25](C(OCC)=O)[CH2:24][CH2:23]2)[C:11](=[O:21])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:6][CH:5]=1>CC(O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:11](=[O:21])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23339044HCID 23339044, compound

Product 1

HCID 23339051HCID 23339051, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred and warm (40° C.) solution of 12 parts of potassium hydroxide in 200 parts of 2-propanol are added at once 21 parts of ethyl 4-{N-(4-chlorophenyl)-N-[(3-methoxyphenyl)acetyl]amino}-1-piperidinecarboxylate and the whole is stirred and refluxed for 17 hours. The reaction mixture is cooled, filtered and evaporated. The semi-solid residue is acidified with a diluted hydrochloric acid solution, washed with 1,1'-oxybisethane and the aqueous acid phase is alkalized with sodium hydroxide solution. The free base is extracted with trichloromethane. The extract is dried and evaporated. The residue is crystallized from a mixture of 1,1'-oxybisethane and hexane, yielding 7.8 parts of N-(4-chlorophenyl)-3-methoxy-N-(4-piperidinyl)benzeneacetamide; mp. 85.7° C.

Workup

  1. stirringthe whole is stirred
  2. temperaturerefluxed for 17 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. customevaporated
  6. washwashed with 1,1'-oxybisethane
  7. extractionThe free base is extracted with trichloromethane
  8. customThe extract is dried
  9. customevaporated
  10. customThe residue is crystallized from a mixture of 1,1'-oxybisethane and hexane

Sources & evidence

ORD record
ord-0215d256fa82436597504a84cc92d44f
Source dataset
uspto-grants-1979_06
Patent number
US04157393

Reaction notes

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