Methane → 1-(4-(Benzyloxy)-3-nitrophenyl)piperazine

HRID 1966486Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:3][C:4]=1[N+:16]([O-:18])=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-bromo-2-nitro-1-[(phenylmethyl)oxy]benzene (3.08 g, 10 mmol) in dioxane (60 ml) was added piperazine (2.58 g, 30 mmol) followed by cesium carbonate (4.8 g, 15 mmol), rac-2,2′ bis(diphenylphosphino)-1,1′-binapthyl (0.311 g, 0.5 mmol) and palladium acetate (0.112 g, 0.5 mmol). The resulting mixture was heated at 100° C. under an atmosphere of argon overnight. The mixture was allowed to cool, charcoal was added and the mixture stirred at room temperature for 30 minutes. The solids were then removed by filtration through celite and the residue washed with ethyl acetate. The filtrate was then reduced in vacuo and the residue was purified by flash column chromatography gave 1-(4-(benzyloxy)-3-nitrophenyl)piperazine which was used for next step without further purification.

Workup

temperatureto cool
customThe solids were then removed by filtration through celite
washthe residue washed with ethyl acetate
customthe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-4aa3a571394b4e1c98d546bc8d7f1ed0
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420640B2

Reaction notes

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