HCID 86742261, compound → HCID 20132436, compound

HRID 845220Notes

Reaction equation

HRID 845220 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH:6]([C:14]2[CH:15]=[C:16]([CH:23]=[CH:24][CH:25]=2)/[CH:17]=[CH:18]/[C:19]([O:21]C)=[O:20])[N:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1>CO.[OH-].[K+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([C:14]2[CH:15]=[C:16]([CH:23]=[CH:24][CH:25]=2)/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[N:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 86742261HCID 86742261, compound

Product 1

HCID 20132436HCID 20132436, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

The ester from above (1.05 g, 2.73 mmol) was dissolved in 20 mL of methanol with 8 mL of 1M potassium hydroxide and stirred overnight at room temperature. The methanol was removed in vacuo and the remaining aqueous solution was extracted with two 15 mL portions of ether. The aqueous layer was adjusted to a pH of 7 with 1M hydrochloric acid. The solution was chilled and the white powdery precipitate was collected by filtration to give 504 mg (46%) of (E)-3-(4-chloro-α-(4-methyl-1-piperazinyl)benzyl)cinnamic acid, m.p. 131°-141°. Calc. for C21H23ClN2O2.2H2O: C, 61.99; H, 6.69; N, 6.88; Cl, 8.71. Found: C, 61.98; H, 6.72; N, 6.89; Cl, 8.66.

Workup

  1. customThe methanol was removed in vacuo
  2. extractionthe remaining aqueous solution was extracted with two 15 mL portions of ether
  3. temperatureThe solution was chilled
  4. filtrationthe white powdery precipitate was collected by filtration

Sources & evidence

ORD record
ord-ed3e99f54e074df78f952d9645a28d95
Source dataset
uspto-grants-1988_07
Patent number
US04757074

Reaction notes

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