1,4-Dioxane hydrochloride → Phenyl[2-(1-piperazinyl)-5-pyrimidinyl]methanone hydrochloride

HRID 522652Notes

Reaction equation

HRID 522652 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[N:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:28].O1CCOCC1>O1CCOCC1>[ClH:28].[C:2]1([C:1]([C:9]2[CH:14]=[N:13][C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[N:11][CH:10]=2)=[O:8])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 118022456Tert-butyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylate

Product 1

HCID 118022636Phenyl[2-(1-piperazinyl)-5-pyrimidinyl]methanone hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylate (1 g, 2.7 mmol) in dioxane (20 mL) was added 4 M HCl-dioxane (20 mL), and the reaction mixture was stirred at room temperature overnight. LCMS showed the reaction was completed. The mixture was directly concentrated to give phenyl(2-(piperazin-1-yl)pyrimidin-5-yl)methanone HCl salt as a yellowish solid (0.95 g, 90%). MS (ES+) C15H16N4O requires: 268, found: 269 [M+H]+.

Workup

  1. concentrationThe mixture was directly concentrated

Sources & evidence

ORD record
ord-99c7400e40b640e8bd6222be1b684379
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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