1,4-Dioxane hydrochloride → 2-[(piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester

HRID 2110000Notes

Reaction equation

HRID 2110000 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].O1CCOCC1.Cl>CO>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 690700652-[(1-tert-butoxycarbonyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester

Product 1

HCID 690679852-[(piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After dissolving 2-[(1-tert-butoxycarbonyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester (2.28 g, 5.87 mmol) in methanol (3 ml), a 4N hydrogen chloride-1,4-dioxane solution (10 ml, 40 mmol) was added and the mixture was stirred at room temperature overnight. The precipitated crystals were filtered out, washed with ethyl acetate and then dried to obtain 2-[(piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester. The compound was identified by LC-MS.

Workup

  1. filtrationThe precipitated crystals were filtered out
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-70750fb8fb4243c88ec8a8aed75e1923
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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