Trifluoroacetic acid → 4-(4-Fluorophenoxy)piperidine

HRID 1714387Notes

Reaction equation

HRID 1714387 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[F:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 50999114Tert-butyl 4-(4-fluorophenoxy)piperidine-1-carboxylate

Product 1

HCID 37348964-(4-Fluorophenoxy)piperidineYield 835.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g (7 mmol) of 4-(4-fluoro-phenoxy)-piperidine 1-carboxylic acid tert-butyl ester was solvated in dichloromethane (12 mL) and trifluoroacetic acid was added at 0° C. (6.17 mL, 54 mmol). The mixture was stirred at room temperature overnight. NaHCO3 was slowly added until pH 9 and the mixture extracted 3 times with dichloromethane and ethyl acetate. The solvent was evaporated to yield 1.81 g (58.5 mmol, 85%) of a white solid that was used without purification on the next steps. MS (m/e): 196.3 (M+H+).

Workup

  1. extractionthe mixture extracted 3 times with dichloromethane and ethyl acetate
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1df508dd19084603ab0620545e57d134
Source dataset
uspto-grants-2010_09
Patent number
US07795437B2

Reaction notes

Loading…