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Sodium Iodide → 1-[2-(Tetrahydropyran-2-yloxy)ethyl]-4-(4-trifluoromethylphenoxy)piperidine

HRID 856018
ノート
印刷プレビュー

反応式

HRID 856018 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.Br[CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[O:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]1[O:21][CH2:20][CH2:19][N:11]1[CH2:10][CH2:9][CH:8]([O:7][C:6]2[CH:14]=[CH:15][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:4][CH:5]=2)[CH2:13][CH2:12]1
参加物反応条件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 5238Sodium IodideHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 36883924-(4-(Trifluoromethyl)phenoxy)piperidine

生成物 1

HCID 230813391-[2-(Tetrahydropyran-2-yloxy)ethyl]-4-(4-trifluoromethylphenoxy)piperidine収率 59.3%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-(4-trifluoromethylphenoxy)-piperidine (1.87 g, 7.63 mmol), 2-(2-bromoethoxy)-tetrahydropyran (1.75 g, 8.4 mmol), potassium carbonate (1.16 g, 8.38 mmol), sodium iodide (1.2 g, 8.01 mmol) in DMF (30 ml) was stirred at 100° C. for 1 hour. The reaction mixture was allowed to return to room temperature, poured into water and extracted with ethyl acetate twice. The extract was washed with water twice and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford 1-[2-(tetrahydropyran-2-yloxy)ethyl]-4-(4-trifluoromethylphenoxy)piperidine (1.69 g, yield 59%) as a colorless oil.

後処理

  1. customto return to room temperature
  2. extractionextracted with ethyl acetate twice
  3. washThe extract was washed with water twice
  4. dry with materialbrine, and dried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

出典と根拠

ORDレコード
ord-5150eea560c240e2a9fbdc981192b314
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07262212B2

反応ノート

読み込み中…

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