Hydrochloric Acid → 4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl-1,3-thiazole-5-carboxylic acid

HRID 561199Notes

Reaction equation

HRID 561199 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17]([O:19]C)=[O:18])=[CH:15][N:16]=2)[CH2:8][CH2:7]1.[OH-].[Na+].Cl>C1COCC1.CO>[F:25][C:2]([F:1])([F:26])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[S:13][C:14]([C:17]([OH:19])=[O:18])=[CH:15][N:16]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57659049Methyl 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carboxylate

Product 1

HCID 666968024-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carboxylate (16 g, 41.4 mmol) and 1 N NaOH (85 mL, 85 mmol) in THF/MeOH (1:1) (v/v) (300 mL) was heated at 80° C. bath for 1 h. Volatile solvents were removed in vacuo. The residue was diluted with H2O, acidified with 1 N HCl (2.2 equiv) and extracted with EtOAc. The EtOAc extract was washed with H2O, dried (Na2SO4) and concentrated to give the title compound as a white solid.

Workup

  1. customVolatile solvents were removed in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with H2O
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82c9c5910d8c4eac8e307bfd800dbac3
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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