1-Fluoro-3-iodo-5-nitrobenzene → 1-(3-Iodo-5-nitrophenyl)-4-(methylsulfonyl)piperazine

HRID 530389Notes

Reaction equation

[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].F[C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([I:21])[CH:13]=1>CS(C)=O.C(OCC)(=O)C>[I:21][C:14]1[CH:13]=[C:12]([N:8]2[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]2)[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=1

Participants

Conditions

Temperature: 130 °C

Procedure

1-(methylsulfonyl)piperazine (627 mg, 3.82 mmol) was added to a solution of 1-fluoro-3-iodo-5-nitrobenzene (510 mg, 1.91 mmol) in dimethylsulfoxide (2 mL). The reaction was heated to 130° C. for 60 minutes in the microwave reaction, then allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate (30 mL) and washed with 1:1 water:brine (3×30 mL). The organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) provided 1-(3-iodo-5-nitrophenyl)-4-(methylsulfonyl)piperazine as a bright yellow foam. 1H NMR (400 MHz, CDCl3) δ 8.04 (s, 1H), 7.70 (s, 1H), 7.51 (s, 1H), 3.42 (s, 8H), 2.87 (s, 3H).

Workup

temperatureto cool to room temperature
washwashed with 1:1 water
dry with materialThe organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-23505cd4440243d5aabca8edd3796ad7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353066B2

Reaction notes

Loading…