Water → HCID 12136657, compound

HRID 2416670Notes

Reaction equation

HRID 2416670 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([O:29][CH3:30])=[C:15]([CH:17]3[CH2:22][CH2:21][N:20](C(=O)C(F)(F)F)[CH2:19][CH2:18]3)[CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([O:29][CH3:30])=[C:15]([CH:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)[CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 12136656HCID 12136656, compound

Product 1

HCID 12136657HCID 12136657, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1-{4-[5-(4-chloro-benzenesulfonyl)2-methoxyphenyl]piperidin-1-yl}-2,2,2-trifluoro-ethanone (31) (77 mg) in methanol (2 mL), a solution of 6N NaOH (0.5 mL) was added. After stirring at 80° C. for 10 min, water was added (10 ml) and the mixture was extracted into ethyl acetate (20 ml). The organic phase was dried (Na2SO4) and concentrated in vacuo to give 4-[5-(4-chloro-benzenesulfonyl)2methoxy-phenyl] piperidine (301) as a white solid (0.054 g ), MS, MH+ 365. The hydrochloride salt was prepared from ethanol-hydrogen chloride, m.p. 235.5-236.0° C.

Workup

  1. extractionthe mixture was extracted into ethyl acetate (20 ml)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28885d7c0e984811aa161152fd130638
Source dataset
uspto-grants-2004_11
Patent number
US06825202B2

Reaction notes

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