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

HRID 900646

Reaction equation

HRID 900646 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-439884e0e9274788b584406ab2659fbe
Source dataset
uspto-grants-2008_04
Patent number
US07361648B2

Linked notes

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