Hydrochloric Acid → N-(4-hydroxyphenyl)-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamide dihydrochloride

HRID 1487738Notes

Reaction equation

HRID 1487738 reaction equation
[ClH:1].O1CCOCC1.OC(C(F)(F)F)=O.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([N:25]2[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][C@@H:26]2[CH2:38][O:39][C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)=[O:24])=[CH:18][CH:17]=1>CO>[ClH:1].[ClH:1].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH:26]2[CH2:38][O:39][C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)=[O:24])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131728855HCID 131728855, compound

Product 1

HCID 66796782N-(4-hydroxyphenyl)-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamide dihydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of (R)-tert-butyl 4-(4-hydroxyphenylcarbamoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate TFA salt (182 mg, 0.335 mmol) in MeOH (1 mL). After 1 h, the reaction mixture was concentrated under reduced pressure, yielding 118 mg (88%) of the title compound as a white solid. LC-MS: RT=2.11 min, [M+H]+=329.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-89c6aa04207348b9badbb621ae94dba1
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Reaction notes

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