1-Methylpiperazine → HCID 20626665, compound

HRID 1241998Notes

Reaction equation

HRID 1241998 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

6

Reactant 4

HCID 531671-MethylpiperazineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 21937437HCID 21937437, compound

Product 1

HCID 20626665HCID 20626665, compoundYield 282.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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 saturated 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

  1. customThe organic phase was partitioned
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in anhydrous THF (16 mL)
  6. stirringThe solution was stirred at 40° C. for 1 h
  7. temperaturecooled
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9940c9bc2e6547eea469fc584ad42c6e
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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