Sodium Hydroxide → 4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoic acid

HRID 1038663Notes

Reaction equation

HRID 1038663 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]=2[C:20]([F:23])([F:22])[F:21])[CH2:4][CH2:3]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[C:20]([F:23])([F:21])[F:22])[CH2:4][CH2:3]1

Participants

4

Reactant 2

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

Product 1

HCID 231458804-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-benzoate (7.23 g, 21.1 mmol, 1.0 eq.) in ethanol (40 ml) is added 1M NaOH (30.6 ml, 30.6 mmol, 1.4 eq.). After stirring for 2 h at room temperature a clear pale yellow solution is obtained. The mixture is evaporated to a volume of 30 ml. Then, the solution is adjusted to pH 7 by addition of 1M HCl and the solvent is stripped off. The residue is taken up three times in toluene (70 ml) and evaporated. The crude material is dissolved in ethanol/THF 1:9 (150 ml), filtered, evaporated, triturated with ethyl acetate, and vacuum dried at 60° C. over night to afford a beige powder: HPLC: tR=3.61 min (purity: >99%, gradient A), ESI-MS: 303.3 [MH]+

Workup

  1. customis obtained
  2. customThe mixture is evaporated to a volume of 30 ml
  3. additionThen, the solution is adjusted to pH 7 by addition of 1M HCl
  4. customevaporated
  5. dissolutionThe crude material is dissolved in ethanol/THF 1:9 (150 ml)
  6. filtrationfiltered
  7. customevaporated
  8. customtriturated with ethyl acetate, and vacuum
  9. customdried at 60° C. over night
  10. customto afford a beige powder

Sources & evidence

ORD record
ord-54b6d96ada1d41bfbd5ab64c41de56bb
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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