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

HRID 36886

반응식

HRID 36886 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2f1d1b5dffd3455f9f2cc1fcb715958f
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418242

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