Cesium carbonate → tert-Butyl 4-(2-methyl-4-nitrophenyl)piperazine-1-carboxylate

HRID 1503830Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[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.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=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: 100 °C

Procedure

A mixture of 1-bromo-2-methyl-4-nitrobenzene (5.16 g, 24 mmol), tert-butyl piperazine-1-carboxylate (4.46 g, 24 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (1.15 g, 2.4 mmol), cesium carbonate (15.65 g, 48 mmol) and tris(dibenzylideneacetone)dipalladium (2.21 g, 2.4 mmol) in 1,4-dioxane (120 mL) was heated at 100° C. for 16 hours. The solid was filtered and the filtrate was concentrated to give the crude product which was purified by flash chromatography on silica gel (200-300 mesh) eluting with 20/1 petroleum ether/ethyl acetate to give the title compound. MS: 322 (M+H+).

Workup

filtrationThe solid was filtered
concentrationthe filtrate was concentrated
customto give the crude product which
customwas purified by flash chromatography on silica gel (200-300 mesh)
washeluting with 20/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record: ord-6d0f4bdc551f464493a90f0dbfa990a3
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212192B2

Reaction notes

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