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Acetonitrile → 1-Benzyl-4-[N-ethyl-N-(6-fluoro-3-nitro-2-pyridyl)amino]piperidine

HRID 361853
ノート
印刷プレビュー

反応式

HRID 361853 の反応式
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][CH2:26][CH3:27])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.CCCCCC>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]([CH2:26][CH3:27])[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[N:3]=2)[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 106088761-benzyl-N-ethylpiperidin-4-amineHCID 113895462,6-Difluoro-3-nitropyridine

生成物 1

HCID 105945621-Benzyl-4-[N-ethyl-N-(6-fluoro-3-nitro-2-pyridyl)amino]piperidine

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 21226206Ethyl acetate hexane溶媒2 回

実験手順

2,6-Difluoro-3-nitropyridine (Recl. Trav. Chim., 95, 127-156 (1976) and Tetrahedron Lett., 28, 111-114 (1987), 2.4 g, 15.0 mmol) and 1-benzyl-4-ethylaminopiperidine (EXAMPLE 11, 3.3 g, 15 mmol) are dissolved in 37.5 mmol of acetonitrile at 0°. Then solid potassium carbonate (2.49 g, 18 mmol) is added and the reaction is slowly warmed to 20°-25°. After the reaction is complete by TLC (ethyl acetate/hexane, (25/75)), it is poured into water and extracted with ethyl acetate. The organic phase is washed with saline, dried over sodium sulfate and concentrated under reduced pressure. Purification via flash column chromatography (5% ethyl acetate/hexane to 10% ethyl acetate/hexane) gives the title compound, mp=99°-100°; NMR (300 MHz, CDCl3) 8.00, 7.13-7.04, 6.02, 3.43, 3.31, 3.28, 2.77, 1.85, 1.71, 1.63 and 0.86δ; CMR (75 MHz, CDCl3) 163.5, 160.2, 151.2, 140.9, 130.4, 128.9, 128.0, 126.9, 96.9, 62.6, 59.6, 52.9, 38.7, 29.3 and 14.0δ.

後処理

  1. temperaturethe reaction is slowly warmed to 20°-25°
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification via flash column chromatography (5% ethyl acetate/hexane to 10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-75ef3697c5524f449a027fc352fcf650
出典データセット
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05866589

反応ノート

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