Hydrochloric Acid → N-Methyl-N-phenyl-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamide dihydrochloride

HRID 70221Notes

Reaction equation

HRID 70221 reaction equation
[ClH:1].O1CCOCC1.OC(C(F)(F)F)=O.[CH3:15][N:16]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:17]([N:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH:20]1[CH2:32][O:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)=[O:18]>CO>[ClH:1].[ClH:1].[CH3:15][N:16]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH:20]1[CH2:32][O:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131728875HCID 131728875, compound

Product 1

HCID 66796915N-Methyl-N-phenyl-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamide dihydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(N-methyl-N-phenylcarbamoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate TFA salt (28.1 mg, 0.052 mmol) in MeOH (1 mL). After 12 h, the reaction mixture was concentrated under reduced pressure, yielding 16.9 mg (81%) of the desired product as a yellow solid. LC-MS: RT=3.83 min, [M+H]+=327.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a49f6fd63a1f4d5bbfc3bb65b997ca82
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

Loading…