Piperidine → N-(4-(1-Piperidinylsulfonyl)phenyl)acetamide

HRID 1787984

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1)(=[O:9])[CH3:8]>O1CCOCC1>[C:7]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:19])=[O:18])=[CH:15][CH:16]=1)(=[O:9])[CH3:8]

Participants

Conditions

Temperature: 80 °C

Procedure

Piperidine (0.0114 Mol) is added to a solution of 4-acetamidophenylsulfonyl chloride (1.34 g, 0.0057 mol) in dioxane (5 mL). The mixture is heated for 1 hour at 80° C., then part of the solvent is removed by evaporation at reduced pressure, and water is added until precipitation of the resulting sulfonamide. The product is collected by filtration as a white solid (52.14% yield) and used without further purification. m.p. 137° C.-139° C. 1H NMR (acetone-d6): δ 1.35-1.43 (m, 2H); 1.52-1.63 (m, 4H); 2.17 (s, 3H); 2.89-2.95 (m, 4H); 7.68-7.70 (d, 2H, J=7); 7.90-7.92 (d, 2H, J=7); 9.55 (bs, 1H). In a similar fashion, the following sulfonamides were prepared:

Workup

custompart of the solvent is removed by evaporation at reduced pressure, and water
additionis added until precipitation of the resulting sulfonamide

Sources & evidence

ORD record: ord-ed8c67e3d1204add98ebb0a1091f6a59
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511133B2

Linked notes

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