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

HRID 70186Notes

Reaction equation

HRID 70186 reaction equation
[ClH:1].O1CCOCC1.[Cl:8][C:9]1[N:14]=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH:18]2[CH2:30][O:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[O:16])[CH:12]=[CH:11][CH:10]=1>>[ClH:8].[ClH:1].[Cl:8][C:9]1[N:14]=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[CH2:30][O:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[O:16])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59671478Tert-butyl 4-(6-chloropicolinoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

Product 1

HCID 86618747(6-Chloropyridin-2-yl)(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)methanone dihydrochlorideYield 91%

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to tert-butyl 4-(6-chloropicolinoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate (90.5 mg, 0.209 mmol). After stirring overnight, the reaction mixture was concentrated under reduced pressure, yielding 77.3 mg (91%) of the title compound. LC-MS: RT=2.86 min, [M+H]+=333.5.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3d98fb8ec64e464ba73a95b90950627e
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

Loading…