Hydrochloric Acid → HCID 178524176, compound

HRID 2110019Notes

Reaction equation

HRID 2110019 reaction equation
C[O:2][C:3]([C:5]1[CH:30]=[CH:29][C:8]2[NH:9][C:10]([NH:12][CH2:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:16][CH2:15]3)=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Li+].Cl.C(OCC)(=O)C>CO>[C:23]1([CH2:22][CH2:21][CH2:20][N:17]2[CH2:16][CH2:15][CH:14]([CH2:13][NH:12][C:10]3[NH:9][C:8]4[CH:29]=[CH:30][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=4[N:11]=3)[CH2:19][CH2:18]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 178497382HCID 178497382, compound

Product 1

HCID 178524176HCID 178524176, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

After suspending 2-{[1-(3-phenyl-propyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-5-carboxylic acid methyl ester (3.2 mmol) in methanol (10 ml), a 4N lithium hydroxide aqueous solution (5.4 ml, 21.4 mmol) was added. The reaction mixture was stirred at 50° C. for 2 hours and then cooled to room temperature. Next, 1N hydrochloric acid was added dropwise to adjust the pH to approximately 6.0. Ethyl acetate (1 ml) was added to the aqueous solution and the mixture was stirred for 3 hours, and then the precipitate was filtered out to obtain 2-{[1-(3-phenyl-propyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-5-carboxylic acid. The compound was identified by LC-MS.

Workup

  1. temperaturecooled to room temperature
  2. stirringthe mixture was stirred for 3 hours
  3. filtrationthe precipitate was filtered out

Sources & evidence

ORD record
ord-5357e18006104a97a5b086f66fce4074
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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