Sodium Iodide → (2-Pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine

HRID 1504166ノート

反応式

HRID 1504166 の反応式
[I-].[Na+].Br[CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:15]=1.C(N(C(C)C)C(C)C)C>O.CN(C=O)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][N:22]([CH2:23][C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)[CH2:4][CH2:5][CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:15]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 60761584(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamine

生成物 1

HCID 66960900(2-Pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Sodium iodide(1.5 g) was added to a DMF solution (20 ml) of 2-(3-bromopropoxy)tetrahydropyran(0.85 ml). The mixture was stirred at 70° C. for 7 hours. The reaction mixture was cooled to room temperature. (2-Pyridin-3-yl-ethyl)-pyridin-4-ylmethyl-amine (1.28 g), and N-ethyldiisopropylamine(1.3 ml) were added thereto. The mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was washed with water and then saturated saline, and dried with anhydrous sodium sulfate. After condensation under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate: methanol=20:1→4:1). The purified product was condensed under reduced pressure to give the title compound(236 mg) as a colorless oily matter.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with water
  5. dry with materialsaturated saline, and dried with anhydrous sodium sulfate
  6. customAfter condensation under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate: methanol=20:1→4:1)
  8. customcondensed under reduced pressure

出典と根拠

ORDレコード
ord-95e2df74697f404baf882308f26d521f
出典データセット
uspto-grants-2015_12
特許番号
US09212187B2

反応ノート

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