Water → HCID 12074216, compound

HRID 1356547Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14](F)=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:21]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N:21]3[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-fluoro-2-nitrophenyl 3-fluorophenyl sulfone (5.00 g, 16.7 mmol), homopiperazine (2.09 g, 20.9 mmol), and potassium carbonate (3.46 g, 25.1 mmol) in 140 mL of dry acetonitrile is stirred vigorously for 4 h at 60° C. After cooling to room temperature, water and CH2Cl2 (140 mL each) are added and the layers separated. The aqueous layer extracted with CH2Cl2 (3×50 mL). The combined organics are dried over MgSO4, filtered, and concentrated to give an orange solid. The crude product is triturated with a hot Et2O:CH2Cl2 mixture (4:1 ) until solid. Further trituration with hot EtOAc/hexane gave 6.31 g (99%) of the title compound as bright yellow solid.

Workup

temperatureAfter cooling to room temperature
customthe layers separated
extractionThe aqueous layer extracted with CH2Cl2 (3×50 mL)
dry with materialThe combined organics are dried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give an orange solid
customThe crude product is triturated with a hot Et2O

Sources & evidence

ORD record: ord-d09d6c276de640d88c6ca240d2c72c69
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586592B2

Reaction notes

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