Sodium Bicarbonate → N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzene sulfonamide

HRID 2470

Reaction equation

HRID 2470 reaction equation
[F:1][C:2]1[CH:43]=[CH:42][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:40][CH3:41])[S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][O:27]C4CCCCO4)=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:40][CH3:41])[S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:12][CH2:13]2)=[O:7])=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 19689959N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-tetrahydropyranyloxymethyl-N-(2-methoxyphenyl)benzene sulfonamide

Product 1

HCID 19689938N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzene sulfonamideYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-tetrahydropyranyloxymethyl-N-(2-methoxyphenyl)benzene sulfonamide (101 mg, 0.165 mmol) was dissolved in methanol (5 ml) to which was subsequently added p-toluenesulfonic acid monohydrate (35 mg, 0.18 mmol) at room temperature. After 2 hour of stirring at the same temperature, methanol was removed by evaporation, and the resulting reaction solution was mixed with saturated sodium bicarbonate aqueous solution (5 ml), extracted with ethyl acetate, and washed with water and saturated brine. The water layer was extracted with ethyl acetate, and washed with water and saturated brine, and the organic layers were combined and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate) to obtain 87 mg (100%) of the title compound in the form of colorless oil.

Workup

  1. customat room temperature
  2. customwas removed by evaporation
  3. customthe resulting reaction solution
  4. extractionextracted with ethyl acetate
  5. washwashed with water and saturated brine
  6. extractionThe water layer was extracted with ethyl acetate
  7. washwashed with water and saturated brine
  8. dry with materialdried on anhydrous sodium sulfate
  9. customThereafter, the solvent was removed by evaporation
  10. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4d1b23c0b5a4476792e51a44f8a8659a
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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