Water → HCID 23565316, compound

HRID 1059341Notes

Reaction equation

HRID 1059341 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[C:17]([O:26][CH3:27])[CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[C:17]([O:26][CH3:27])[CH:16]=2)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 18670203HCID 18670203, compound

Product 1

HCID 23565316HCID 23565316, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.41 g of methyl 4-(1-benzyl-4-hydroxypiperidin-4-yl)-2-methoxyphenylacetate was dissolved in 50 ml of toluene. After adding 3.5 g of p-toluenesulfonic acid monohydrate, the mixture was heated under reflux for 1 hour and 45 minutes. After adding water and triethylamine, the reaction mixture was extracted with dichloromethane and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, 3.6 g of a pale yellow oily substance was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour and 45 minutes
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure, 3.6 g of a pale yellow oily substance
  6. customwas obtained

Sources & evidence

ORD record
ord-6deaa67f5bd042dfbc1bb870cbac16a2
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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