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

HRID 562029

Reaction equation

HRID 562029 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-e3c06bea0b0c42e3b1cc8fcc7ab25cad
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Linked notes

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