Trifluoroacetic acid → 4-(2-Chloro-5-methylphenoxy)piperidine

HRID 2185485Notes

Reaction equation

HRID 2185485 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=2[Cl:29])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[Cl:29][C:23]1[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=1[O:21][CH:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22458419n-Tert-butoxycarbonyl-4-(2-chloro-5-methylphenoxy)piperidine

Product 1

HCID 171951004-(2-Chloro-5-methylphenoxy)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6 mL) was added to a solution of N-tert-butoxycarbonyl-4-(2-chloro-5-methylphenoxy)piperidine (A, 489 mg) in dichloromethane (20 mL) at room temperature. After stirring at room temperature for 30 min, the reaction mixture was evaporated in vacuo. The residue was partitioned between chloroform and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo to give the titled compound as yellow crystals, which was used in the next reaction without her purification.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe residue was partitioned between chloroform and saturated sodium hydrogen carbonate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9341a83b03f24b8db2017f6ac3f78e00
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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