Potassium Carbonate → tert-Butyl 4-(1-(3-methoxy-4-nitrophenyl)piperidin-4-yl)piperazine-1-carboxylate

HRID 1255993Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([O:30][CH3:31])[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:31][O:30][C:23]1[CH:22]=[C:21]([N:1]2[CH2:6][CH2:5][CH:4]([N:7]3[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]3)[CH2:3][CH2:2]2)[CH:26]=[CH:25][C:24]=1[N+:27]([O-:29])=[O:28]

Participants

Conditions

Temperature: 90 °C

Procedure

tert-Butyl 4-(piperidin-4-yl)piperazine-1-carboxylate (1.842 g, 6.84 mmol) was added to a stirring mixture of 4-fluoro-2-methoxy-1-nitrobenzene (1.17 g, 6.84 mmol) and K2CO3 (2.83 g, 20.51 mmol) in acetonitrile (15 mL) and the reaction mixture was stirred at 90° C. for 15 h. The reaction mixture was filtered and concentrated in vacuo. The crude residue was purified by chromatography on silica gel (hexanes/EtOAc) to give the title product (2.5 g, 87%). m/z 421.

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated in vacuo
customThe crude residue was purified by chromatography on silica gel (hexanes/EtOAc)

Sources & evidence

ORD record: ord-5a8c79292a2e4246a5897d7a1034f9e2
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461170B2

Reaction notes

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