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

HRID 580856Notes

Reaction equation

CS([O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.O[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>[CH2:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([O:5][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)[CH2:7][CH2:8]1)=[O:13])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1-(ethoxycarbonyl)piperidin-4-yl methanesulfonate (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

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

Sources & evidence

ORD record: ord-44e69b9cd31743c9a4964aa2d84a8d97
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05919782

Reaction notes

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