1-Methylpiperazine → 1-Methyl-4-(3-nitro-4-pyridyl)piperazine

HRID 524857Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>O1CCOCC1.CCOC(C)=O>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 80 °C

Procedure

4-chloro-3-nitro-pyridine (2 g, 12.61 mmol) in dioxane (15 mL) was treated with 1-methylpiperazine (1.515 g, 1.678 mL, 15.13 mmol) and DIPEA (2.445 g, 3.295 mL, 18.92 mmol). The mixture was stirred at 80° C. for 1 hour, cooled to RT. The mixture was partioned between EtOAc and an aqueous saturated solution of NaHCO3 (40 ml). Combined organic extract was dried over MgSO4 and concentrated under reduced pressure to give an orange oil which was purified by chromatography on silica eluting with 5-10% MeOH/EtOAc/0.5-1% NH4OH to give 1-methyl-4-(3-nitro-4-pyridyl)piperazine 14 as a deep yellow oil which crystallised on standing. (2.56 g, 11.52 mmol, 91.36%). MS (ES+) 223.4.

Workup

temperaturecooled to RT
extractionCombined organic extract
dry with materialwas dried over MgSO4
concentrationconcentrated under reduced pressure
customto give an orange oil which
customwas purified by chromatography on silica eluting with 5-10% MeOH/EtOAc/0.5-1% NH4OH

Sources & evidence

ORD record: ord-13bf62e9aafb484a99b6a3547a3cc20f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340546B2

Reaction notes

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