Piperazine → Phenyl 5-(1-piperazinyl)-2-pyridinyl sulfone

HRID 23874

Reaction equation

[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13](Cl)=[CH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>N1C=CC=CC=1>[N:17]1([C:13]2[CH:14]=[CH:15][C:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[N:11][CH:12]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of 5-chloro-2-pyridinyl phenyl sulfone (10.2 g, 40.2 mmol) in pyridine (100 mL) was added piperazine (13.8 g, 161 mmol). The mixture was heated to 120° C. in a preheated oil bath for 18 h. The mixture then was removed from heat and cooled to room temperature. The mixture was partitioned between water and ethyl acetate. The layers were separated and the organic layer washed twice with water (2×50 mL). The organic layer was dried with anhydrous magnesium sulfate and concentrated. The solids obtained after concentration were recrystallized from water and dried to give 5.89 g of the title compound; m.p. 126-127° C.; IR (drift) 1568, 1479, 1447, 1306, 1290, 1254, 1175, 1154, 1145, 1104, 830, 756, 715, 688, 602 cm−1. 1H NMR (CDCl3) δ 3.0, 3.29, 7.13, 7.53, 8.01, 8.26.

Workup

customThe mixture then was removed
temperaturefrom heat
temperaturecooled to room temperature
customThe mixture was partitioned between water and ethyl acetate
customThe layers were separated
washthe organic layer washed twice with water (2×50 mL)
dry with materialThe organic layer was dried with anhydrous magnesium sulfate
concentrationconcentrated
customThe solids obtained
concentrationafter concentration
customwere recrystallized from water
customdried

Sources & evidence

ORD record: ord-8d80402db955440c94de8d01b68f81b7
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855709B2

Linked notes

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