Benzyltrimethylammonium hydroxide → HCID 74062991, compound

HRID 1059340Notes

Reaction equation

HRID 1059340 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=O)=[C:17]([O:23][CH3:24])[CH:16]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26]([CH2:28][S:29]([CH3:31])=O)=[O:27].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCCC1.CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[C:28]([S:29][CH3:31])[S:26]([CH3:25])=[O:27])=[C:17]([O:23][CH3:24])[CH:16]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 3016865Di(methanesulfinyl)methaneHCID 18670605HCID 18670605, compound

Product 1

HCID 74062991HCID 74062991, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.43 g of 4-(1-benzyl-4-hydroxypiperidin-4-yl)-2-methoxybenzaldehyde was dissolved in 30 ml of tetrahydrofuran. To the resulting solution were added 2.42 ml of methyl methylsulfinylmethyl sulfoxide and 2 ml of a 40% solution of benzyltrimethylammonium hydroxide in methanol and the resulting mixture was heated under reflux for 3 hours. After concentrating the reaction mixture, water was added thereto followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 4.58 g of the title compound as a pale yellow oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationAfter concentrating the reaction mixture, water
  4. additionwas added
  5. extractionthereto followed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-08ee1d36349d44c3af57343188238f03
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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