1,4-Dioxane hydrochloride → 2-{[(4-Fluoro-4-piperidyl)methyl]amino}benzimidazole-5-carboxylic acid methyl ester hydrochloride

HRID 2112550Notes

Reaction equation

HRID 2112550 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([F:29])([CH2:14][NH:15][C:16]2[NH:17][C:18]3[CH:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:30].O1CCOCC1>CO>[ClH:30].[CH3:28][O:27][C:25]([C:23]1[CH:22]=[CH:21][C:19]2[N:20]=[C:16]([NH:15][CH2:14][C:11]3([F:29])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[NH:17][C:18]=2[CH:24]=1)=[O:26]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 690670954-Fluoro-4-({[5-(methoxycarbonyl)benzimidazol-2-yl]amino}methyl)piperidinecarboxylic acid tert-butyl ester

Product 1

HCID 690664572-{[(4-Fluoro-4-piperidyl)methyl]amino}benzimidazole-5-carboxylic acid methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After dissolving 4-fluoro-4-({[5-(methoxycarbonyl)benzimidazol-2-yl]amino}methyl)piperidinecarboxylic acid tert-butyl ester (1.2 g, 2.95 mmol) in MeOH (6 ml), a 4N hydrogen chloride/1,4-dioxane solution (3.7 ml, 14.7 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated to obtain 2-{[(4-fluoro-4-piperidyl)methyl]amino}benzimidazole-5-carboxylic acid methyl ester hydrochloride. The compound was identified by LC-MS.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d2b3d539f2ca4185a859fd9bfbb85df8
Source dataset
uspto-grants-2009_04
Patent number
US07524841B2

Reaction notes

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