Trifluoroacetic acid → 4-(4-Chlorophenyl)-4-methoxypiperidine

HRID 556988Notes

Reaction equation

HRID 556988 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([O:14][CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]2([O:14][CH3:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 219975781-Tert-butoxycarbonyl-4-(4-chlorophenyl)-4-methoxypiperidine

Product 1

HCID 224946584-(4-Chlorophenyl)-4-methoxypiperidineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Chloro-phenyl)-4-methoxy-piperidine-1-carboxylic acid tert-butyl ester (0.108 g, 0.331 mmol) was dissolved in methylene chloride (6 mL) and cooled in an ice bath. Trifluoroacetic acid (2 mL) was added slowly dropwise. The mixture was stirred for 2 hr as it warmed to room temperature. The reaction mixture was concentrated in vacuo and then redissolved in methylene chloride and washed with saturated sodium bicarbonate (2×10 mL). The pooled aqueous layers were extracted with methylene chloride (2×10 mL). The methylene chloride extracts were pooled, dried over magnesium sulfate, filtered and concentrated in vacuo to give 4-(4-Chloro-phenyl)-4-methoxy-piperidine as a clear oil (72 mg, 97%).

Workup

  1. temperaturecooled in an ice bath
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionredissolved in methylene chloride
  4. washwashed with saturated sodium bicarbonate (2×10 mL)
  5. extractionThe pooled aqueous layers were extracted with methylene chloride (2×10 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6a839358fb04625bd50ba681234e019
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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