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

HRID 1184161Notes

Reaction equation

HRID 1184161 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-af34dd53f24849d9ba892988bd0637a4
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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