Trifluoroacetic acid → 4-(4-Chloro-phenyl)-3-methyl-piperidin-4-ol

HRID 242557Notes

Reaction equation

HRID 242557 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([OH:14])[CH:10]([CH3:22])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2([OH:14])[CH2:12][CH2:13][NH:8][CH2:9][CH:10]2[CH3:22])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59444243Tert-butyl 4-(4-chlorophenyl)-4-hydroxy-3-methylpiperidine-1-carboxylate

Product 1

HCID 231370704-(4-Chloro-phenyl)-3-methyl-piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-Chloro-phenyl)-4-hydroxy-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (1.5 g, 4.6 mmol) in dichloromethane (40 mL) at about 0° C. was added trifluoroacetic acid (10 mL). The solution was stirred for about 2 hours. The solvent was evaporated and the residue was dissolved in ethyl acetate. The solution was neutralized with saturated sodium bicarbonate, and washed with brine and dried over magnesium sulfate. The solvent was removed to give a yellow solid. No purification was needed.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed
  6. customto give a yellow solid
  7. customNo purification

Sources & evidence

ORD record
ord-5f03b08838ed4fd68cc2e8906fe403f8
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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