1-Methylpiperazine → 3-(4-Methylpiperazin-1-yl)-5-nitropyridin-4-amine

HRID 1472189Notes

Reaction equation

HRID 1472189 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[NH2:8].[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>CCOC(C)=O.O>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=2[NH2:8])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 49975884-Amino-3-bromo-5-nitropyridine

Product 1

HCID 866983293-(4-Methylpiperazin-1-yl)-5-nitropyridin-4-amineYield 56.9%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

A solution of 3-bromo-5-nitropyridin-4-amine (LXIX) (618 mg, 2.83 mmol) in 1-methylpiperazine (1 mL, 8.51 mmol) was heated at 140° C. overnight. The reaction was poured into an EtOAc/H2O mixture; the organic layer was separated, dried over MgSO4 and concentrated under vacuum. The crude product was purified on a silica gel column (100% CHCl3→3:97 MeOH(7N NH3):CHCl3) to give 3-(4-methylpiperazin-1-yl)-5-nitropyridin-4-amine (CXVII) as a yellow solid (382 mg, 1.61 mmol, 56.7% yield). 1H NMR (CDCl3, 500 MHz,) δ ppm 2.20 (s, 3H), 2.35-2.37 (m, 4H), 4.52-3.54 (m, 4H), 5.96 (s, 1H), 7.42 (s, 2H), 8.78 (s, 1H); ESIMS found C10H15N5O2 m/z 238 (M+H).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified on a silica gel column (100% CHCl3→3:97 MeOH(7N NH3):CHCl3)

Sources & evidence

ORD record
ord-e1969f3dcd984e18b059217d618cf58c
Source dataset
uspto-grants-2015_04
Patent number
US09012472B2

Reaction notes

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