Hydrochloric Acid → (6-Phenylpyridin-2-yl)(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)methanone dihydrochloride

HRID 70188Notes

Reaction equation

HRID 70188 reaction equation
[ClH:1].O1CCOCC1.[C:8]1([C:14]2[N:19]=[C:18]([C:20]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH:23]3[CH2:35][O:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[ClH:1].[ClH:1].[C:8]1([C:14]2[N:19]=[C:18]([C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH:23]3[CH2:35][O:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59671588Tert-butyl 4-(6-phenylpicolinoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

Product 1

HCID 66797115(6-Phenylpyridin-2-yl)(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)methanone dihydrochlorideYield 99%

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-(6-phenylpicolinoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate (143 mg, 0.231 mmol) in MeOH (1 mL). After stirring overnight, the reaction mixture was concentrated under reduced pressure, yielding 102.1 mg (99%) of the title compound. LC-MS: RT=4.36 min, [M+H]+=375.6.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7dd338372db546a385a60f273496ecb3
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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