Pyridine → HCID 58266521、化合物

HRID 1888425ノート

反応式

HRID 1888425 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([OH:16])[CH:5]=[C:6]([Cl:15])[C:7]=1[CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.N1C=CC=CC=1.[F:23][C:24]([F:30])([F:29])[S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([O:16][S:25]([C:24]([F:30])([F:29])[F:23])(=[O:27])=[O:26])[CH:5]=[C:6]([Cl:15])[C:7]=1[CH2:8][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

参加物

5

反応物 3

HCID 1049PyridineHCID 79000Trifluoromethanesulfonyl chlorideHCID 582665303,5-Dichloro-4-piperidin-1-ylmethylphenol

生成物 1

HCID 58266521HCID 58266521、化合物収率 77.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of 3,5-dichloro-4-piperidin-1-ylmethylphenol (290 mg, 1.1 mmol) and pyridine (0.36 mL, 4.5 mmol) in DCM (10 mL) at −20° C. was added trifluoromethanesulfonyl chloride (0.38 mL, 2.2 mmol). After the addition was complete the reaction was allowed to warm to ambient temperature and stirred for 10 minutes. The mixture was diluted with DCM (20 mL), washed with water (10 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in cyclohexane) to afford the title compound as a colourless oil (334 mg, 76%). 1H NMR (CDCl3, 300 MHz): 7.26 (s, 2H), 3.66 (s, 2H), 2.53-2.44 (m, 4H), 1.58-1.48 (m, 4H), 1.50-1.34 (m, 2H).

後処理

  1. additionAfter the addition
  2. washwashed with water (10 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-79a69f966050483eb946bba504c5b284
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

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