Hydrochloric Acid → HCID 66731937, compound

HRID 1963283Notes

Reaction equation

HRID 1963283 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH3:12])=[O:10])[CH:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:4]1)#N.OO.[OH-:26].[K+].Cl.[OH2:29]>CCOC(C)=O>[CH3:12][O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:3]([C:1]([OH:29])=[O:26])[CH2:4][CH:5]1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[O:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 14797Potassium HydroxideHCID 66732043HCID 66732043, compound

Product 1

HCID 66731937HCID 66731937, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-cyano-2-(4-(trifluoromethyl)benzyl)piperidine-1-carboxylate (2.1 g, 6.44 mmol), hydrogen peroxide (5 mL, 206.78 mmol) and potassium hydroxide (3.61 g, 54.36 mmol) in water (50 mL) were heated to 80° C. overnight. 1 M HCl and EtOAc was added to the reaction mixture. The organic phase was isolated, dried with Na2SO4, filtered through Celite and the solvent was evaporated to yield 1-(methoxycarbonyl)-2-(4-(trifluoromethyl)benzyl)-piperidine-4-carboxylic acid (1.67 g, 75%).

Workup

  1. customThe organic phase was isolated
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered through Celite
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c7666d7708ad49958cf12c49f292ef70
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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