Hydrochloric Acid → N-[(3S,5R)-5-(1-hydroxypropyl)piperidin-3-yl]-1-(4-methoxybutyl)-N-(2-methylpropyl)-1H-benzimidazole-2-carboxamide dihydrochloride

HRID 1509491Notes

Reaction equation

HRID 1509491 reaction equation
[OH:1][CH:2]([C@@H:5]1[CH2:10][C@H:9]([N:11]([C:16]([C:18]2[N:22]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[C:21]3[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=3[N:19]=2)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)[CH2:3][CH3:4].[ClH:40]>C(O)C>[ClH:40].[ClH:40].[OH:1][CH:2]([C@H:5]1[CH2:6][NH:7][CH2:8][C@@H:9]([N:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[C:16]([C:18]2[N:22]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[C:21]3[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=3[N:19]=2)=[O:17])[CH2:10]1)[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67321555tert-butyl (3R,5S)-3-(1-hydroxypropyl)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-1-carboxylate

Product 1

HCID 67321867N-[(3S,5R)-5-(1-hydroxypropyl)piperidin-3-yl]-1-(4-methoxybutyl)-N-(2-methylpropyl)-1H-benzimidazole-2-carboxamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (3R,5S)-3-(1-hydroxypropyl)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-1-carboxylate (200 mg) in ethanol (1 ml) was added 12M hydrochloric acid (0.30 ml), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethanol, and ethanol was evaporated under reduced pressure. This operation was repeated twice to give the object product (140 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol
  3. customethanol was evaporated under reduced pressure

Sources & evidence

ORD record
ord-86e2e61159aa48909a59860bc9967fc0
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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