Hydrochloric Acid → HCID 23145857, compound

HRID 1465009Notes

Reaction equation

HRID 1465009 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=2[C:19]([F:22])([F:21])[F:20])[CH2:4][CH2:3]1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[C:19]([F:20])([F:21])[F:22])[CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67359917HCID 67359917, compound

Product 1

HCID 23145857HCID 23145857, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-(1-methylpiperidine-4-yloxy)-3-(trifluoromethyl)benzoate (512 mg, 1.61 mmol) was dissolved in a mixture of THF (1.5 mL), MeOH (1.5 mL) and H2O (1.5 mL), and then NaOH (193 mg, 4.84 mmol) was added thereto. The reaction mixture was stirred at 90° C. for 22 hours and cooled to room temperature, and 1N HCl was added dropwise thereto to pH 4. The reaction mixture was concentrated, and a mixed solvent (DCM/MeOH=5/1) was added thereto. The remaining solid was filtered, and the filtrate was concentrated to obtain the title compound (391 mg, 80%) without further purification.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. additiona mixed solvent (DCM/MeOH=5/1) was added
  4. filtrationThe remaining solid was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bb1bce41eaf74230ab1a9d19073fc347
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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