Potassium Hydroxide → 2-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]carbonylaminomethyl]piperidin-1-yl]benzoic acid

HRID 602157Notes

Reaction equation

HRID 602157 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]4[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=4[C:26]([O:28]C)=[O:27])[CH2:19]3)=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]4[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=4[C:26]([OH:28])=[O:27])[CH2:19]3)=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58992629Methyl 2-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]carbonylaminomethyl]piperidin-1-yl]benzoate

Product 1

HCID 115764122-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]carbonylaminomethyl]piperidin-1-yl]benzoic acidYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]carbonylaminomethyl]piperidin-1-yl]benzoate (29.5 mg, 0.0609 mmol) was dissolved in methanol (3 mL). To this solution, a 1 mol/L aqueous potassium hydroxide solution (0.183 mL, 0.183 mmol) was added and the mixture was stirred for 2 hours while being refluxed. Subsequently, the reaction mixture was concentrated and water was added to the residue, followed by 2 mol/L hydrochloric acid to make the mixture acidic. The crystallized powdery product was collected by filtration and washed with water to give 23.2 mg (81%) of the desired product as a colorless powder.

Workup

  1. temperaturewhile being refluxed
  2. concentrationSubsequently, the reaction mixture was concentrated
  3. additionwater was added to the residue
  4. filtrationThe crystallized powdery product was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-472b51ab6fc54c459ecde9f682f2a998
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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