Water → 4-(1-Benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenethyl alcohol

HRID 1059318Notes

Reaction equation

HRID 1059318 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][O:23]COC)=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][OH:23])=[CH:19][CH:20]=2)=[CH:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 186702071-Benzyl-4-[4-[2-(methoxymethoxy)ethyl]phenyl]piperidin-4-ol

Product 1

HCID 221264074-(1-Benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenethyl alcoholYield 24.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1.0 g of 1-benzyl-4-[4-[2-(methoxymethoxy)ethyl]phenyl]piperidin-4-ol in 30 ml of toluene was added 2.0 g of p-toluenesulfonic acid. Then the resulting mixture was heated under reflux for 1 hour while eliminating the water thus formed with a Dean Stark trap. Then the reaction mixture was brought back to room temperature and a saturated aqueous solution of sodium bicarbonate was added thereto. Then it was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.2 g of the title compound as a brown oily substance.

Workup

  1. temperatureThen the resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customthus formed with a Dean Stark trap
  4. customwas brought back to room temperature
  5. extractionThen it was extracted with ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationAfter distilling off the solvent under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8acf607fccdb4e748bb2d28d3ad1f2c1
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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