Water → HCID 20070542, compound

HRID 981596Notes

Reaction equation

HRID 981596 reaction equation
[H-].[Na+].[C:3]1(=[O:9])[NH:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.[OH2:18]>CN(C=O)C>[O:9]=[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([N:8]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1=[O:18])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 126652-PiperidoneHCID 24758Sodium hydride

Product 1

HCID 20070542HCID 20070542, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 50% oil suspension of sodium hydride (3.16 grams, 65 mmol) in 60 mL dry DMF under nitrogen was added 6.53 grams (65 mmol) of delta-valerolactam. The mixture was stirred overnight. Then, 4.0 grams (16.3 mmol) of 1,6-dibromohexane was added, and the mixture was stirred for an additional six hours. Two hundred mL of water was added, and the aqueous phase was extracted with chloroform. The organic layer was washed with water and dried over magnesium sulfate, and the solvent was removed in vacuo. Fractional distillation afforded 1.9 gram (41%) of pure material as an oil, boiling point 160° C. (0.1 torr).

Workup

  1. stirringthe mixture was stirred for an additional six hours
  2. extractionthe aqueous phase was extracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. distillationFractional distillation

Sources & evidence

ORD record
ord-5c9623676e4a4e7fbac330541033c9f9
Source dataset
uspto-grants-1991_02
Patent number
US04992472

Reaction notes

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