1-Methylpiperazine → 1-(2-METHOXY-4-NITROPHENYL)-4-METHYLPIPERAZINE

HRID 2384890Notes

Reaction equation

HRID 2384890 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 118446211-(2-METHOXY-4-NITROPHENYL)-4-METHYLPIPERAZINEYield 78.4%

Procedure

Heat 1-chloro-2-methoxy-4-nitro-benzene (1.0 g, 5.33 mmol) and 1-methylpiperazine (1.33 g, 13.30 mmol) at 100° C. in a sealed tube for 16 h. Cool the mixture to room temperature and partition between dichloromethane (50 mL) and water (50 mL). Separate the organic portion and extract the aqueous portion with dichlorormethane (2×20 mL). Dry the combined organic portions (Na2SO4), filter and concentrate in vacuo to give 1.05 g (78%) of the title compound. MS/ES m/z 252.0 [M+H]+.

Workup

  1. custompartition between dichloromethane (50 mL) and water (50 mL)
  2. customSeparate the organic portion
  3. extractionextract the aqueous portion with dichlorormethane (2×20 mL)
  4. dry with materialDry the combined organic portions (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-dfb0e585a60a4f03b9f8d37c265ac6e8
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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