Iodoethane → N-ethyl-N-(1-(4-formylphenyl)piperidin-4-yl)acetamide

HRID 591640Notes

Reaction equation

HRID 591640 reaction equation
[H-].[Na+].[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:20])[CH3:19])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].[CH2:21](I)[CH3:22]>CN(C=O)C>[CH2:21]([N:17]([CH:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:7]=[CH:6][C:5]([CH:3]=[O:4])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1)[C:18](=[O:20])[CH3:19])[CH3:22]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86662017N-(1-(4-formylphenyl)piperidin-4-yl)acetamide

Product 1

HCID 86662019N-ethyl-N-(1-(4-formylphenyl)piperidin-4-yl)acetamideYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 60% suspension in oil of NaH (0.113 g, 2.8 mmol) was added to a 0° C. solution of N-(1-(4-formylphenyl)piperidin-4-yl)acetamide (0.700 g, 2.8 mmol) in DMF (10 mL) and stirred for 35 minutes. To this mixture was added EtI (0.23 mL, 2.8 mmol) and the reaction was warmed to room temperature for 2 hours, quenched 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 0% to 5% MeOH/CH2Cl2, afforded N-ethyl-N-(1-(4-formylphenyl)piperidin-4-yl)acetamide (0.490 g, 64%).

Workup

  1. customquenched with H2O
  2. extractionextracted with EtOAc
  3. washThe organics were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel
  8. washeluting with 0% to 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1b96d8b669a241f1977a51cc0fbb4dd6
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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