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

HRID 1034427

Reaction equation

HRID 1034427 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Bromophenylhydrazine hydrochloride (11.5 g) is solubilized in a solution of 1,1-dimethylethyl 4-[(2-oxopropyl)thio]piperidine-1-carboxylate (prepared in Example 10) 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).

Workup

  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

Sources & evidence

ORD record
ord-e510e489d86545898b603bf74b9401e4
Source dataset
uspto-grants-1994_05
Patent number
US05317025

Linked notes

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