Potassium Carbonate → tert-Butyl 4-(2-bromo-4-nitrophenyl)piperazine-1-carboxylate

HRID 541956Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-bromo-1-fluoro-4-nitrobenzene (0.1 g, 0.45 mmol) and tert-butyl piperazine-1-carboxylate (85 mg, 0.45 mmol) in N,N-dimethylformamide (0.9 mL) was treated with potassium carbonate (94 mg, 0.68 mmol) and stirred at 20° C. for 23 h and at 60° C. for 3.5 h. The reaction mixture was diluted with water (10 mL) and ethyl acetate (20 mL). The organic layer was separated, washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give a yellow oil. This material was purified by flash column chromatography to give the desired product (0.15 g, 87%) as a yellow solid. LCMS for C15H20BrN3O4Na (M+Na)+: m/z=407.9, 410.1.

Workup

customThe organic layer was separated
washwashed with water (10 mL) and brine (10 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated
customto give a yellow oil
customThis material was purified by flash column chromatography

Sources & evidence

ORD record: ord-af3052012ea1464fa30e41c4ef18a86f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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