Hydrochloric Acid → [3-[3,5-Dimethyl-4-(6-trifluoromethyl benzothiazole-2-yl)piperazine-1-ylmethyl]phenyl]acetic acid

HRID 420579Notes

Reaction equation

HRID 420579 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]2[CH2:17][CH:16]([CH3:18])[N:15]([C:19]3[S:20][C:21]4[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:14]([CH3:32])[CH2:13]2)[CH:6]=1.[OH-].[Na+].Cl>CO>[CH3:18][CH:16]1[N:15]([C:19]2[S:20][C:21]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:22]=3[N:23]=2)[CH:14]([CH3:32])[CH2:13][N:12]([CH2:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66657824HCID 66657824, compound

Product 1

HCID 66657881[3-[3,5-Dimethyl-4-(6-trifluoromethyl benzothiazole-2-yl)piperazine-1-ylmethyl]phenyl]acetic acidYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [3-[3,5-dimethyl-4-(6-trifluoromethyl benzothiazole-2-yl)piperazine-1-ylmethyl]phenyl]acetic acid methyl ester (171 mg), 2N sodium hydroxide (1 mL) and methanol (2 mL) was stirred at room temperature for 1 hour. The mixture was neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (82 mg). Yield: 52%.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-9e17f773bee5466e9e6f365586ce5b36
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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