Trifluoroacetic acid → 4-(3,4-Dichlorobenzyl)piperidine

HRID 1250523Notes

Reaction equation

HRID 1250523 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[Cl:29][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[Cl:28])[CH2:21][CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 222577171-(Tert-butoxycarbonyl)-4-(3,4-dichlorobenzyl)piperidine

Product 1

HCID 37695634-(3,4-Dichlorobenzyl)piperidineYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (50 ml) was added to a solution of 1-(tert-butoxycarbonyl)-4-(3,4-dichlorobenzyl)piperidine (24 g, 69.7 mmol) in methylene chloride (150 ml) and the reaction mixture was stirred for 1 h. The solvent was removed under reduced pressure, followed by addition of ethyl acetate (200 ml), and the resulting mixture was made basic with 1N aqueous sodium hydroxide. The organic layer was separated, dried over magnesium sulfate and the solvent was removed under reduced pressure to give 4-(3,4-dichlorobenzyl)piperidine (17.1 g) as light brown solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionfollowed by addition of ethyl acetate (200 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e50e1d09a2e94f628c21b331ef368da2
Source dataset
uspto-grants-2002_01
Patent number
US06339087B1

Reaction notes

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