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Water → 1-(2-Chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol

HRID 1161664
ノート
印刷プレビュー

反応式

HRID 1161664 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1.C(N(CC)CC)C.O>C(O)CCC>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([N:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[N:7]=1.[Cl:1][C:2]1[N:7]=[C:6]([N:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=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 962WaterHCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 2415542,4-Dichloro-6-phenylpyrimidine

生成物 2

HCID 586260781-(2-Chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-olHCID 586261271-(4-Chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
120 °C

実験手順

A mixture of compound, 2,4-dichloro-6-phenyl-pyrimidine (13 g, 57.77 mmol), piperidin-4-ol (2.9 g, 28.88 mmol) and triethylamine (32.14 mL, 231.11 mmol) in butanol (110 mL) was stirred at 120° C. for 12 hours under nitrogen atmosphere. The reaction mixture was then poured into water (250 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were collected, combined, washed with water (50 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum. The residue thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to give the two compounds, 1-(4-chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol and 1-(2-chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol in ratio 1:4 (overall yield: 51%).

後処理

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. customThe organic layers were collected
  3. washwashed with water (50 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-58b9974ee23e462f936c2eca623109c8
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07820654B2

反応ノート

読み込み中…

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