Hydrochloric Acid → 2-[(1-tert-butoxycarbonyl-piperidin-4-ylmethlyl)-amino]-1H-benzimidazole-4-carboxylic acid

HRID 2110002Notes

Reaction equation

C[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:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[OH-].[Li+].Cl>CO>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:16]([CH:15]=[N:14][C:11]2[NH:10][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=3[N:12]=2)[CH2:17][CH2:18]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 50 °C

Procedure

After dissolving 2-[(1-tert-butoxycarbonyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester (5.47 g, 14.1 mmol) in methanol (60 ml), an aqueous lithium hydroxide solution (4 mol/L, 20 ml, 80 mmol) was added and the mixture was stirred at 50° C. overnight. The reaction mixture was cooled in an ice bath, and 6N hydrochloric acid (5 ml) was added dropwise. Stirring was continued for 1 hour in an ice bath while gradually adding 1N hydrochloric acid to adjust the pH to approximately 7.5. The precipitate was filtered out and washed with ethyl acetate and water. It was then dried under reduced pressure to obtain 2-[(1-tert-butoxycarbonyl-piperidin-4-ylmethlyl)-amino]-1H-benzimidazole-4-carboxylic acid. The compound was identified by LC-MS.

Workup

temperatureThe reaction mixture was cooled in an ice bath
stirringStirring
waitwas continued for 1 hour in an ice bath
filtrationThe precipitate was filtered out
washwashed with ethyl acetate and water
customIt was then dried under reduced pressure

Sources & evidence

ORD record: ord-5df3032dc45249b0be149d9f683243da
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517875B2

Reaction notes

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