Hydrochloric Acid → 5-bromo-2-methyl-3-(piperidin-4-ylthio)-1H-indole

HRID 36886

反応式

HRID 36886 の反応式
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.O=[C:12]([CH3:28])[CH2:13][S:14][CH:15]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]1.Cl.CCOCC>C(O)(C)C>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]([CH3:28])=[C:13]2[S:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 121574-Bromophenylhydrazine hydrochlorideHCID 199366031,1-Dimethylethyl 4-[(2-oxopropyl)thio]piperidine-1-carboxylate

生成物 1

HCID 99053425-bromo-2-methyl-3-(piperidin-4-ylthio)-1H-indole収率 57%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

4-Bromophenylhydrazine hydrochloride (11.5 g) is solubilized in a solution of 1,1-dimethylethyl 4-[(2-oxopropyl)thio]piperidine-1-carboxylate (14 g, prepared in Example 11) in isopropanol (100 ml) under nitrogen. The solution is cooled to 0° C. and saturated with gaseous hydrogen chloride. After 4 hours at room temperature, the precipitate is filtered off, taken up in sodium hydroxide and extracted with ether and then with methylene chloride. The organic phases are combined, dried over sodium sulfate and concentrated. The solid obtained is taken up in the minimum amount of ether and recrystallized from xylene to give 5-bromo-2-methyl-3-(piperidin-4-ylthio)-1H-indole (9.5 g).

後処理

  1. filtrationthe precipitate is filtered off
  2. extractionextracted with ether
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe solid obtained
  6. customrecrystallized from xylene

出典と根拠

ORDレコード
ord-2f1d1b5dffd3455f9f2cc1fcb715958f
出典データセット
uspto-grants-1995_05
特許番号
US05418242

関連ノート

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