Hydrochloric Acid → 2-fluoro-N-methyl-4-(3-(piperidin-4-yl)pyrazin-2-yl)benzamide trihydrochloride

HRID 2364569Notes

Reaction equation

HRID 2364569 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13]([CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[N:14][CH:15]=[CH:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:11])[NH:9][CH3:10].[ClH:31].O1CCOCC1>CO>[ClH:31].[ClH:31].[ClH:31].[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:14][CH:15]=[CH:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]([NH:9][CH3:10])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86705402Tert-butyl 4-(3-(3-fluoro-4-(methylcarbamoyl)phenyl)pyrazin-2-yl)piperidine-1-carboxylate

Product 1

HCID 867054032-fluoro-N-methyl-4-(3-(piperidin-4-yl)pyrazin-2-yl)benzamide trihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a RBF was added tert-butyl 4-(3-(3-fluoro-4-(methylcarbamoyl)phenyl)pyrazin-2-yl)piperidine-1-carboxylate (2.40 g, 5.79 mmol) and methanol (20 mL) was added 4M HCl in dioxane (5 mL, 20.00 mmol). The solution was stirred at room temperature. After 96 h, the reaction was concentrated in vacuo to give 2-fluoro-N-methyl-4-(3-(piperidin-4-yl)pyrazin-2-yl)benzamide trihydrochloride (2.46 g, 5.81 mmol, 100% yield), as a yellow foam. The 3 HCl equivalent was determined from the weight of the compound, without further characterization.

Workup

  1. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-b2943f5de8d24fbab9c6977432afd437
Source dataset
uspto-grants-2014_04
Patent number
US08691986B2

Reaction notes

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