Potassium Hydroxide → 4-{[3-(4-Chlorophenyl)propyl](ethyl)amino}benzoic acid

HRID 1154357Notes

Reaction equation

HRID 1154357 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:23][CH3:24])[C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:23][CH3:24])[C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 442788674-[[3-(p-Chlorophenyl)propyl]ethylamino]benzoic acid, ethyl ester

Product 1

HCID 442788794-{[3-(4-Chlorophenyl)propyl](ethyl)amino}benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.0 g. portion of 4-[[3-(p-chlorophenyl)propyl]ethylamino]benzoic acid, ethyl ester is dissolved in 50 ml. of 95% ethanol. A 4.0 g. portion of potassium hydroxide is added, and the solution is refluxed overnight. The solution is filtered, then diluted with 100 ml. of water, and adjusted to pH 6.5 with 37% hydrochloric acid. This mixture is extracted with two 50 ml. portions of dichloromethane, which are combined, washed with 50 ml. of water, and evaporated to an oil. This oil is chromatographed on a silica gel column, eluting with chloroform, followed by 10% ethyl acetate in chloroform. The ethyl acetate-chloroform eluate is crystallized from ethanol, giving 700 mg. of the desired product as a tan solid.

Workup

  1. temperaturethe solution is refluxed overnight
  2. filtrationThe solution is filtered
  3. additiondiluted with 100 ml
  4. extractionThis mixture is extracted with two 50 ml
  5. washwashed with 50 ml
  6. customof water, and evaporated to an oil
  7. customThis oil is chromatographed on a silica gel column
  8. washeluting with chloroform
  9. customThe ethyl acetate-chloroform eluate is crystallized from ethanol
  10. customgiving 700 mg

Sources & evidence

ORD record
ord-504c3bf9b5e848b785e426e10ead6457
Source dataset
uspto-grants-1984_12
Patent number
US04489094

Reaction notes

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