Hydrochloric Acid → 5-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide hydrochloride

HRID 1806217Notes

Reaction equation

HRID 1806217 reaction equation
[ClH:1].[NH2:2][C:3]([C:5]1[CH:6]=[C:7]([Br:27])[CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[C:10]2[CH:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]1)=[O:4]>O1CCOCC1.CO>[ClH:1].[Br:27][C:7]1[CH:8]=[C:9]2[C:13](=[C:5]([C:3]([NH2:2])=[O:4])[CH:6]=1)[NH:12][CH:11]=[C:10]2[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59600660tert-butyl 4-(5-bromo-7-carbamoyl-1H-indol-3-yl)piperidine-1-carboxylate

Product 1

HCID 667232845-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4M solution of HCl in dioxane (194 mL) was added to a solution of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indol-3-yl]-1-piperidinecarboxylate (10 g, 23.7 mmol) in methanol (50 mL). The reaction mixture was stirred at room temperature for 4 hours, and the solvent was evaporated under reduced pressure to give the title compound (9.5 g), which was used in the next step without further purification.

Workup

  1. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ad2927ff06a04765967ace7ce1f06aaf
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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