Water → HCID 18670605, compound

HRID 1059339Notes

Reaction equation

HRID 1059339 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([OH:23])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[CH:6][C:5]=1[O:24][CH3:25].C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(N(CC)CC)C>[CH2:16]([N:13]1[CH2:12][CH2:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:3]=[O:2])=[C:5]([O:24][CH3:25])[CH:6]=2)([OH:23])[CH2:15][CH2:14]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 18670147HCID 18670147, compound

Product 1

HCID 18670605HCID 18670605, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 10.0 g of 4-(1-benzyl-4-hydroxypiperidin-4-yl)-2-methoxybenzaldehyde dimethyl acetal were added 100 ml of toluene and 6.15 g of p-toluenesulfonic acid monohydrate and the resulting mixture was heated under reflux for 1 hour. To the reaction mixture were added water and triethylamine 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 3.43 g of the title compound as a pale brown oily substance.

Workup

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

Sources & evidence

ORD record
ord-4291507b43764f5cb6d4131f395b6f12
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…