Trifluoroacetic acid → 4-[4-(4-Trifluoromethylbenzyloxy)benzyl]piperidine

HRID 2172221Notes

Reaction equation

HRID 2172221 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:32][C:29]([F:30])([F:31])[C:26]1[CH:25]=[CH:24][C:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:16][CH:17]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70873664HCID 70873664, compound

Product 1

HCID 708737824-[4-(4-Trifluoromethylbenzyloxy)benzyl]piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{4-[4-(Trifluoromethyl)benzyloxy]benzyl}piperidine-1-carboxylic acid tert-butyl ester (2.64 g, 5.9 mmol), dichloromethane (5 ml) and trifluoroacetic acid (5 ml) were mixed and stirred at room temperature for 2 hours. After concentrating the reaction mixture, dichloromethane was added to the residue, and 5 N sodium hydroxide was further added, followed by vigorous stirring. The organic layer was separated, washed with water, dried over sodium sulfate, and then concentrated to afford the title compound as a colorless powder (2.06 g, 100%).

Workup

  1. concentrationAfter concentrating the reaction mixture, dichloromethane
  2. additionwas added to the residue, and 5 N sodium hydroxide
  3. additionwas further added
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7276781d11e443218db8a544a285f034
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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