Trifluoroacetic acid → HCID 66835932, compound

HRID 2404429Notes

Reaction equation

HRID 2404429 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:25]([O:24][C:22](=[O:23])[CH:15]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67512170HCID 67512170, compound

Product 1

HCID 66835932HCID 66835932, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(Ethoxycarbonyl-phenyl-methoxy)-piperidine-1-carboxylic acid tert-butyl ester (3.4 g) in dichloromethane (25 mL) is added trifluoroacetic acid (18 mL). After 30 minutes at room temperature, the volatiles are removed under reduced pressure. Water (30 mL) is added and the solution is basified by adding a solution of saturated sodium carbonate to pH 10. The aqueous phase is extracted with dichloromethane. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure to give (1-methylpiperidin-4-yloxy)phenylacetic acid ethyl ester used without further purification.

Workup

  1. customthe volatiles are removed under reduced pressure
  2. additionWater (30 mL) is added
  3. additionby adding a solution of saturated sodium carbonate to pH 10
  4. extractionThe aqueous phase is extracted with dichloromethane
  5. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1df79ea4c7b849f28690a4f5f0ff70bb
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

Loading…