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

HRID 396335ノート

反応式

HRID 396335 の反応式
[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

参加物

7

反応物 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 64909601-Benzyl-3-ethylpiperidin-4-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fa84d4909e204876ada75d2f233342d8
出典データセット
uspto-grants-2003_08
特許番号
US06608078B2

反応ノート

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