Water → 1-Benzyl-3,5-dimethyl-3-ethyl-4-piperidone

HRID 396335노트

반응식

HRID 396335 반응식
[CH2:1]([N:8]1[CH2:13]C[C:11](=O)[CH:10](CC)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:19]I.O.[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:9][CH:10]([CH3:11])[C:26](=[O:22])[C:25]([CH3:19])([CH2:24][CH3:23])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 64909601-Benzyl-3-ethylpiperidin-4-one

생성물 1

HCID 222788971-Benzyl-3,5-dimethyl-3-ethyl-4-piperidone

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

1-Benzyl-3-ethyl-piperidin-4-one (33 g, 152.0 mmole) was added to the stirred suspension of sodium hydride (9.5 g, 200.0 mmole) in tetrahydrofuran (300 ml) at 32° C. and stirring was continued for 1 hr. Methyl iodide (30 ml, 490.0 mmole) in dry tetrahydrofuran (100 ml) was added it at 0-5° C. The resulting mixture stirred at room temperature for 4 hr, water (100 ml) and ethyl acetate (800 ml) were added respectively. Organic layer was separated, dried (Na2SO4) and concentrated to give crude product, which was purified through column chromatography. Elute from 10% ethyl acetate in hexane afforded 1-benzyl-3,5-dimethyl-3-ethylpiperidin-4-one. Yield 22.0 g (59%), C16H23NO, m/z 246 (M+1).

후처리

  1. stirringThe resulting mixture stirred at room temperature for 4 hr
  2. customOrganic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customwas purified through column chromatography
  7. washElute from 10% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-fa84d4909e204876ada75d2f233342d8
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608078B2

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