Sodium hydride → 1-(2,2-Dimethoxyethyl)-piperidin-2-one

HRID 10183

반응식

HRID 10183 반응식
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].Cl[CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[H-].[Na+]>C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][N:5]1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 740895-Chlorovaleryl chlorideHCID 89728Aminoacetaldehyde dimethyl acetal

생성물 1

HCID 219785091-(2,2-Dimethoxyethyl)-piperidin-2-one수율 80.9%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 10340Sodium Carbonate용매

실험 절차

To a stirred mixture of aminoacetaldehyde dimethylacetal (0.74 g, 7 mmole) in ethyl acetate (20 mL) and 2M sodium carbonate (20 mL) was added 5-chlorovaleryl chloride (1.55 g, 10 mmole). The reaction mixture was stirred at ambient temperature for 1 hour. The aqueous layer was separated and extracted with ethyl acetate. The combined organic phase was washed with 1% hydrochloric acid and water, dried (magnesium sulfate), and concentrated. The oily residue was dissolved in tetrahydrofuran, and sodium hydride (60% in oil) (0.3 g, 7.5 mmole) was added. The reaction mixture was heated under reflux for 1.5 hours and filtered. The filtrate was concentrated to give 1-(2,2-dimethoxyethyl)-piperidin-2-one (1.06 g) as a pale yellow oil.

후처리

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase was washed with 1% hydrochloric acid and water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. dissolutionThe oily residue was dissolved in tetrahydrofuran
  7. temperatureThe reaction mixture was heated
  8. temperatureunder reflux for 1.5 hours
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-1a741121a16944648d852fb3d307e1e8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094778B2

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