1-[2-(piperidin-1-yl)ethyl]-1H-benzimidazol-2-amine → 2-Amino-3-(5-bromo-2-thenoylmethyl)-1-(2-piperidinoethyl)-benzimidazole hydrobromide

HRID 54696

Reaction equation

HRID 54696 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](=[O:10])[CH2:8]Br)=[CH:4][CH:3]=1.[NH2:11][C:12]1[N:16]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:15]2[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=2[N:13]=1>CCOCC.CC(C)=O>[BrH:1].[NH2:11][CH:12]1[N:16]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:15]2[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=2[N:13]1[CH2:8][C:7](=[O:10])[C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 5665591-[2-(piperidin-1-yl)ethyl]-1H-benzimidazol-2-amineHCID 19883982-Bromo-1-(5-bromothiophen-2-yl)ethan-1-one

Product 1

HCID 190408912-Amino-3-(5-bromo-2-thenoylmethyl)-1-(2-piperidinoethyl)-benzimidazole hydrobromideYield 82%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

Add a solution of 5-bromo-2-bromoacetylthiophene (5.68 g, 20 mmol) in 30 ml of ether to a hot solution of 2-amino-1-(2-piperidinoethyl)-benzimidazole (4.88 g, 20 mmol) in 150 ml of acetone. Stir and maintain at room temperature for five hours. Suction-filter the precipitate, wash with acetone and then with ether to obtain the title compound.

Workup

  1. filtrationSuction-filter the precipitate
  2. washwash with acetone

Sources & evidence

ORD record
ord-3561e4cfe32445759c3dc24690ee59e2
Source dataset
uspto-grants-1997_04
Patent number
US05623073

Linked notes

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