Dimethylformamide → Tert-butyl 4-[4-(5-chloro-2-nitrophenoxy)phenyl]piperazine-1-carboxylate

HRID 1373260Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[O:31][C:28]1[CH:29]=[CH:30][C:25]([N:22]2[CH2:23][CH2:24][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:20][CH2:21]2)=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-2-fluoronitrobenzene (2.63 g, 15 mmols), 4-(4-tert-butoxycarbonylpiperazin-1-yl)phenol (4.18 g, 15 mmols), potassium carbonate (2.07 g, 15 mmols) and N,N-dimethylformamide (50 ml) was stirred at 100° C. for 12 hours. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The residue was purified through silica gel column chromatography to give a crystal of tert-butyl 4-[4-(5-chloro-2-nitrophenoxy)phenyl]piperazine-1-carboxylate (5.8 g, 89%).

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried with anhydrous magnesium sulfate
customthe solvent was evaporated away
customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record: ord-c22043a04e964c2884385748d8cbf5e7
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160887B1

Reaction notes

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