Sodium Hydroxide → HCID 42641877, compound

HRID 2382185Notes

Reaction equation

HRID 2382185 reaction equation
[C:1]1([N:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([O:17]CC)=[O:16])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([N:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68735485HCID 68735485, compound

Product 1

HCID 42641877HCID 42641877, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-(4-(phenyl(3-(trifluoromethyl)phenyl)amino)piperidin-1-yl)-acetate (1.1 g, 3 mmol) and sodium hydroxide 1N (4 ml, 4 mmol) in MeOH (15 mL) was heated to 70° C. with stirring for 2 h. Upon cooling to RT, the solvent was removed under reduced pressure. The residue was dissolved in water and the pH adjusted to 4 with 2 N HCl. The solution was extracted with DCM. The DCM layers were combined, dried (Na2SO4), and concentrated. The residue was purified with ISCO using 0-15% MeOH in DCM to give 2-(4-(phenyl(3-(trifluoromethyl)phenyl)amino)piperidin-1-yl)acetic acid (0.8 g, 78% yield). MS (ESI, pos. ion) m/z: 379.1 (M+1).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionThe solution was extracted with DCM
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified with ISCO

Sources & evidence

ORD record
ord-0837034e9ee148f1bd380d224816e8df
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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