1-Methylpiperazine → HCID 20626665, compound
Reaction equation
[CH2:1]([NH:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:2].ClC(Cl)(O[C:18](=[O:24])OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+].[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C(Cl)(Cl)Cl>[CH2:1]([NH:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:18]([N:35]2[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]2)=[O:24])=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 100 mL flask was added 4-ethylamino-3-nitroaniline (625 mg, 3.45 mmol), chloroform (30 mL), and triphosgene (341 mg, 1.15 mmol). To the solution was added satd NaHCO3 (30 mL), and the biphasic mixture was stirred for 30 min. The organic phase was partitioned, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in anhydrous THF (16 mL), and 4-methylpiperizine (291 mg, 2.90 mmol) was added. The solution was stirred at 40° C. for 1 h, cooled and concentrated under reduced pressure to provide the title compound (1.0 g, 94%) as a red solid. 1H-NMR (CDCl3): δ 7.91 (1H, d), 7.84 (1H, t), 7.61 (1H, dd), 6.95 (1H, s), 6.73 (1H, d) 3.52 (4H, t), 3.31 (2H, m), 2.42 (4H, t), 2.32 (3H, s), 1.34 (3H, t); MS(ESI): 308 (MH+).
Workup
- customThe organic phase was partitioned
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in anhydrous THF (16 mL)
- stirringThe solution was stirred at 40° C. for 1 h
- temperaturecooled
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6db07d60dd0443668a208c27cbfd9f5e
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696473B2
Reaction notes
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