Diisopropylethylamine → 4-(8-Azabicyclo[3.2.1]oct-8-yl)-3-fluorobenzonitrile

HRID 586069

反応式

HRID 586069 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].Cl.[CH:12]12[NH:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2.C(N(C(C)C)CC)(C)C>CS(C)=O.[Cl-].[Na+].O>[CH:16]12[N:19]([C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[F:1])[CH:12]([CH2:18][CH2:17]1)[CH2:13][CH2:14][CH2:15]2

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 5222728-Azabicyclo[3.2.1]octane hydrochlorideHCID 5872033,4-Difluorobenzonitrile

生成物 1

HCID 223376114-(8-Azabicyclo[3.2.1]oct-8-yl)-3-fluorobenzonitrile

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
120 °C

実験手順

3,4-Difluorobenzonitrile (1.75 g; 25.1 mmol), 8-aza-bicyclo[3.2.1]octane hydrochloride (2.1 g; 13.8 mmol), and diisopropylethylamine (3.2 g; 25.1 mmol), were combined in DMSO (30 mL) and heated at 120° C. overnight. The mixture was allowed to cool to ambient temperature, poured into brine (75 mL), and extracted with diethyl ether (2×50 mL). The organics were combined, dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was filtered through a pad of silica gel (ethyl acetate as eluent) to provide the title compound. 1H NMR (DMSO-d6) δ 7.69 (dd, 1H), 7.42 (dd, 1H), 7.15 (t, 1H), 4.41 (s, 2H), 1.98 (m, 2H), 1.62-1.86 (m, 5H), 1.41 (m, 3H); MS (ESI) m/z 231, (M+H)+.

後処理

  1. temperatureto cool to ambient temperature
  2. extractionextracted with diethyl ether (2×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. filtrationThe residue was filtered through a pad of silica gel (ethyl acetate as eluent)

出典と根拠

ORDレコード
ord-2f27ceb37fd64d3a84af97a43a74da87
出典データセット
uspto-grants-2005_08
特許番号
US06933311B2

関連ノート

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