Hydrochloric Acid → 4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoic acid

HRID 1184848Notes

Reaction equation

HRID 1184848 reaction equation
C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[C:7]([C:19]([F:22])([F:21])[F:20])[CH:6]=1)C.[OH-].[Na+].Cl>C(O)C>[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:23])=[O:3])=[CH:6][C:7]=2[C:19]([F:22])([F:20])[F:21])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23145917Ethyl 4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoate

Product 1

HCID 231458804-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoic acidYield 104%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-benzoic acid ethyl ester 37 (21 mg, 0.064 mmol) in ethanol (5 mL) was added 2N NaOH (0.318 mL, 0.636 mmol). The resulting mixture was stirred at rt for 2 h. The reaction mixture was acidified with 2N HCl solution and concentrated in vacuo to give the crude 4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-benzoic acid 38 (20 mg, 104%) which was used without further purification.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bf4be6a6b5e43209bb7393ed60a1c97
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

Loading…