Diisopropylethylamine → Tert-butyl 4-(3,4-dinitrophenyl)-3-methylpiperazine-1-carboxylate

HRID 415116

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][CH:15]1[NH:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O>[N+:11]([C:4]1[CH:3]=[C:2]([N:20]2[CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH:15]2[CH3:14])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])([O-:13])=[O:12]

Participants

Conditions

Temperature: 50 °C

Procedure

4-Fluoro-1,2-dinitrobenzene (0.93 g, 5.0 mmol, commercially available from Oakwood Products) and tert-butyl 3-methylpiperazine-1-carboxylate (1.0 g, 5.0 mmol) were dissolved in 3 mL of DMA, and 3 mL of diisopropylethylamine was added. The mixture was stirred at 50° C. overnight, and then cooled to room temperature, separated between ethyl acetate and water. The combined organic were washed with water, brine, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was separated by silica gel column (20% to 40% ethyl acetate in hexanes) to give 1.0 g of tert-butyl 4-(3,4-dinitrophenyl)-3-methylpiperazine-1-carboxylate. 1H-NMR (400 MHz, CDCl3): δ 8.05 (d, 2H), 6.84 (m, 2H), 3.90-4.10 (m, 3H), 3.05-3.60 (m, 4H), 1.50 (s, 9H), 1.10 (s, 3H). MS (EI): 367 (MH+).

Workup

temperaturecooled to room temperature
customseparated between ethyl acetate and water
washThe combined organic were washed with water, brine
dry with materialdried with anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was separated by silica gel column (20% to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-db0ed36138b04b8ca6901f55354d3b4c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088767B2

Linked notes

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