Potassium Carbonate → N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide

HRID 591790Notes

Reaction equation

HRID 591790 reaction equation
BrC[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH:18]([N:21]([CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:22](=[O:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH:8]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][N:28]2[CH2:29][CH2:30][CH:25]([N:21]([CH:18]([CH3:20])[CH3:19])[C:22](=[O:24])[CH3:23])[CH2:26][CH2:27]2)=[CH:11][CH:10]=1)=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110851354-(2-Bromoethyl)benzaldehydeHCID 23369939N-isopropyl-N-(piperidin-4-yl)acetamide

Product 1

HCID 86662036N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamideYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(bromoethyl)benzaldehyde (0.840 g, 4.2 mmol) and K2CO3 (1.75 g, 12.6 mmol) in DMF (15 mL) was added N-isopropyl-N-(piperidin-4-yl)acetamide (0.92 g, 4.2 mmol) and the reaction was stirred at room temperature 5 hours, then concentrated in vacuo. The resulting mixture was diluted with H2O and extracted with EtOAc. The organics were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, afforded N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide (0.770 g, 61%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe resulting mixture was diluted with H2O
  3. extractionextracted with EtOAc
  4. washThe organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 1% to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-510d241cc99b49c193ede95e9eabbcd2
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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