Potassium Carbonate → N-(1-(4-formylphenyl)piperidin-4-yl)acetamide

HRID 591639Notes

Reaction equation

HRID 591639 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].F[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:16]([C:15]1[CH:18]=[CH:19][C:12]([N:8]2[CH2:9][CH2:10][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][CH2:7]2)=[CH:13][CH:14]=1)=[O:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 14451564-Acetamidopiperidine

Product 1

HCID 86662017N-(1-(4-formylphenyl)piperidin-4-yl)acetamideYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-acetamidopiperidine (2.5 g, 17.5 mmol) in DMF (10 mL) was added 4-fluorobenzaldehyde (2.2 g, 17.5 mmol) and K2CO3 (2.9 g, 21.2 mmol). The reaction was heated at 120° C. for 4 hours, diluted with H2O, and extracted with EtOAc. The organics were washed sequentially with H2O and brine, dried (Na2SO4), filtered, and concentrated in vacuo, to afford N-(1-(4-formylphenyl)piperidin-4-yl)acetamide (3.1 g, 92%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed sequentially with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f37b113e2fb74b13a59cc7a8b53d2778
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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