1-Methylpiperazine → HCID 68686602, compound

HRID 2262661Notes

Reaction equation

HRID 2262661 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[C:10](Br)[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])[CH3:2].[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[C:10]([N:21]2[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]2)[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])[CH3:2]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 53419413Ethyl (5-bromo-2-nitrophenyl)acetate

Product 1

HCID 68686602HCID 68686602, compound

Conditions

Temperature
65 °C

Procedure

Under argon, a mixture of [5-bromo-2-nitro-phenyl]acetic acid ethyl ester (2.02 g, 7.00 mmol) and 1-methyl-piperazine (1.40 g, 14.0 mmol) is heated at 65° C. for 24 h. The reaction mixture is partitioned between CH2Cl2 (25 mL) and H2O (25 mL), and the aqueous layer is extracted with CH2Cl2 (2×25 mL). The combined organic layers are washed with brine (25 mL), dried over Na2SO4, and concentrated at reduced pressure. The crude product is purified by FCC(CH2Cl2/MeOH 97.5:2.5) to afford the title compound as a yellow oil. ES+-MS: 308 [M+H]+.

Workup

  1. customThe reaction mixture is partitioned between CH2Cl2 (25 mL) and H2O (25 mL)
  2. extractionthe aqueous layer is extracted with CH2Cl2 (2×25 mL)
  3. washThe combined organic layers are washed with brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated at reduced pressure
  6. customThe crude product is purified by FCC(CH2Cl2/MeOH 97.5:2.5)

Sources & evidence

ORD record
ord-a7517b5afbe548d0a52f7d68c152d1b8
Source dataset
uspto-grants-2010_12
Patent number
US07851475B2

Reaction notes

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