Water → HCID 66649765, compound

HRID 419653Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].[CH3:13][O:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:13][O:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:7]2[CH:6]=[CH:5][C:4]([N+:10]([O-:12])=[O:11])=[C:3]([O:2][CH3:1])[CH:8]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-fluoro-2-(methyloxy)-1-nitrobenzene (which may be prepared according to Example 22, step A) (1 g, 5.8 mmol) in 15 mL of DMSO was added, 1-[2-(methyloxy)ethyl]piperazine (0.92 g, 6.4 mmol), and K2CO3 (2.4 g, 17.4 mmol). The mixture was heated to 80° C. overnight. The mixture was then poured into 100 mL of H2O and extracted with EtOAc, washed with a saturated NaCl solution, dried over Na2SO4, filtered and rotovapped to dryness to give 1.8 g of crude 1-[2-(methyloxy)ethyl]-4-[3-(methyloxy)-4-nitrophenyl]piperazine. MS (ESI): 296 [M+H]+. This material was dissolved in 15 mL EtOH and 1 mL DMF in a 100 mL round bottom flask. Platinum on Carbon (5% by weight) (0.2 g) was added and the flask was flushed with N2. After about 15 min, a balloon containing H2 was added and the N2 was removed. H2 was bubbled through the solution for a few minutes. The reaction mixture was let stir overnight under balloon pressure. In the morning the balloon was removed and the flask flushed with N2 to remove all H2. The solution was filtered through celite and evaporated to afford the title compound of step A (1.49 g, 5.62 mmol, 92%); MS (ESI): 266 [M+H]+.

Workup

extractionextracted with EtOAc
washwashed with a saturated NaCl solution
dry with materialdried over Na2SO4
filtrationfiltered

Sources & evidence

ORD record: ord-e7b025ec3bc245ef84bb18b8837bec52
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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