Potassium Carbonate → N-Methyl-4-[4-(4-pyridyl)piperazin-1-yl]benzenesulphonamide

HRID 2232407

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[CH3:13][NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=1)(=[O:17])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[CH3:13][NH:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]([N:10]2[CH2:9][CH2:8][N:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:12][CH2:11]2)=[CH:22][CH:23]=1)(=[O:16])=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(4-pyridyl)piperazine (0.86 g), N-methyl-4-fluorobenzenesulphonamide (1.00 g) and potassium carbonate (2.00 g) in N-methylpyrrolidone was stirred at 100° C. for 24 hours and then evaporated. The residue was partitioned between dichloromethane and 2N hydrochloric acid. The acid layer was washed with dichloromethane, filtered and made basic with sodium bicarbonate solution. The mixture was extracted several times with chloroform, and the combined extracts were washed with water, dried over magnesium sulphate and evaporated. The residue was crystallised from ethanol/ethyl acetate to give the title compound (0.12 g), m.p. 204°-206° C. Found: C,57.55; H,6.13; N,16.62. C16H20N4O2S requires: C,57.81; H,6.06; N,16.85%.

Workup

customevaporated
customThe residue was partitioned between dichloromethane and 2N hydrochloric acid
washThe acid layer was washed with dichloromethane
filtrationfiltered
extractionThe mixture was extracted several times with chloroform
washthe combined extracts were washed with water
dry with materialdried over magnesium sulphate
customevaporated
customThe residue was crystallised from ethanol/ethyl acetate

Sources & evidence

ORD record: ord-542a1ec6e4ad4a5d9140fb585b095058
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788196

Linked notes

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