Triethylamine → (3,4-Dinitrophenyl)-(4-methylpiperazin-1-yl)methanone

HRID 535812Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=O)([O-:3])=[O:2].O=S(Cl)Cl.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CCN(CC)CC>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]([N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)=[O:9])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])([O-:3])=[O:2]

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of 3,4-dinitrobenzoic acid (10.6 g, 50 mmol) and SOCl2 (50 mL) was heated at reflux for 6 hrs. Then the mixture was evaporated to dryness in vacuo. The residue was dissolved in CH2Cl2 (50 mL) and cooled to 5° C. To this solution, N-methylpiperazine (5.5 g, 55 mmol) and Et3N (5.5 g, 55 mmol) were added dropwise as a solution in CH2Cl2 (50 mL). After stirring overnight at rt, the combined organic phase was washed with water (100 mL), dried over Na2SO4, filtered and concentrated, the resulting residue was purified by silica gel chromatography (eluent: 5% MeOH in CH2Cl2) to give a yellow solid (14.0 g, 95.2%). 1H NMR (300 MHz, DMSO-d6) δ: 8.29 (1H, s), 8.25-8.27 (1H, d, J=9.0 Hz), 7.95-7.98 (1H, d, J=9.0 Hz), 3.62 (2H, m), 3.28 (2H, m), 2.38 (2H, m), 2.26 (2H, m), 2.19 (3H, s).

Workup

temperaturewas heated
temperatureat reflux for 6 hrs
customThen the mixture was evaporated to dryness in vacuo
dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
washthe combined organic phase was washed with water (100 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customthe resulting residue was purified by silica gel chromatography (eluent: 5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-a06e1215cf5e4dc4af568b9c1a0654be
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859553B2

Reaction notes

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