Enantholactam → 1-Pent-4-enyl-azocan-2-one

HRID 433069

Reaction equation

HRID 433069 reaction equation
[H-].[Na+].[NH:3]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:11].Br[CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17]>CN(C)C=O>[CH2:17]([N:3]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:11])[CH2:16][CH2:15][CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 12657EnantholactamHCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-

Product 1

HCID 219785471-Pent-4-enyl-azocan-2-oneYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of sodium hydride (0.9 g, 37.5 mmole) in dimethylformamide (50 mL) was added azocan-2-one (3.83 g, 30 mmole). The mixture was stirred at room temperature for 15 minutes, and then 5-bromo-1-pentene (5.03 g, 33.7 mmole) was added slowly. The reaction mixture was stirred at room temperature for 30 minutes, and then at 80° C. for 16 hours. The solvent was removed under reduced pressure and water was added to the residue. The mixture was extracted with ethyl ether, the organic phase was washed with water, dried (magnesium sulfate) and concentrated to give 1-pent-4-enyl-azocan-2-one (5.53 g,) as an oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. waitat 80° C. for 16 hours
  3. customThe solvent was removed under reduced pressure and water
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with ethyl ether
  6. washthe organic phase was washed with water
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5cd3faaf42d842908600841ceb54943e
Source dataset
uspto-grants-2003_12
Patent number
US06667301B2

Linked notes

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