4-Hydroxybenzaldehyde → 4-[N-(Ethoxycarbonyl)-4-piperidinyloxy]benzaldehyde

HRID 2392548Notes

Reaction equation

HRID 2392548 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9](CS([O-])(=O)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][CH:9]([O:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 18980161N-(ethoxycarbonyl)-piperidine-4-methanesulphonate

Product 1

HCID 189801644-[N-(Ethoxycarbonyl)-4-piperidinyloxy]benzaldehydeYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of N-(ethoxycarbonyl)-piperidine-4-methanesulphonate (10 g) and 4-hydroxy benzaldehyde (5.8 g) in dry DMF (75 ml), K2CO3 (11 g) was added and the mixture was stirred at 80° C. for 12 h. At the end of this time, the reaction mixture was cooled, added water and extracted with EtOAc. The EtOAc extract was washed with 5% aqueous Na2CO3 solution followed by brine and dried over anhydrous sodium sulphate. The solvent was then removed by distillation under reduced pressure to give 7 g (63.6%) of the title compound as a semi solid.

Workup

  1. additionwas added
  2. temperatureAt the end of this time, the reaction mixture was cooled
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with 5% aqueous Na2CO3 solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-fbdf6cfe138c462d9b05af40046419f9
Source dataset
uspto-grants-1998_09
Patent number
US05801173

Reaction notes

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