Sodium Hydroxide → HCID 23112486, compound

HRID 501330Notes

Reaction equation

HRID 501330 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[F:27])[O:15]C)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CC(C)=O.Cl>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][C:18]=2[F:27])=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58817534HCID 58817534, compound

Product 1

HCID 23112486HCID 23112486, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of the 1-benzyl-4-[(2-fluoro-4-trifluoromethyl-phenyl)-methoxy-methylene]-piperidine (9.9 g, 26.1 mmol) in acetone (100 mL) and conc. HCl (10 mL) in a sealed vessel was heated at 60° C. for 2 hours. Upon cooling to room temperature the solution was basified with the addition of 3 N NaOH. The resulting mixture was extracted with EtOAc (2×200 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4), filtered and evaporated yielding 8.8 g (92%) of the desired product as a solid.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×200 mL)
  2. washThe combined extracts were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d77693358aa445f3b524cd3e1be2710b
Source dataset
uspto-grants-2010_08
Patent number
US07772252B2

Reaction notes

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