Piperonylamine → 5-[4-(4-Oxo-piperidine-1-sulfonyl)-benzyl]-thiazolidine-2,4-dione

HRID 2300225Notes

Reaction equation

HRID 2300225 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=2)[S:3]1.Cl.O.[NH:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1>>[O:27]=[C:24]1[CH2:25][CH2:26][N:21]([S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:8][CH:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 2723901PiperonylamineHCID 156164324-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]benzene-1-sulfonyl chloride

Product 1

HCID 187677925-[4-(4-Oxo-piperidine-1-sulfonyl)-benzyl]-thiazolidine-2,4-dione

Procedure

The title compound was prepared from 4-(2,4-dioxo-thiazolidin-5-ylmethyl)-benzene-sulfonylchloride (J. Med. Chem. 1992, 35, 1853) and 4-piperidone monohydrate hydrochloride according to the procedure of Intermediate 22 as a white solid; 1H NMR (300 MHz, DMSO-d6) □ 2.40-2.50 (m, 4 H), 3.20-3.40 (m, 5 H), 3.50 (dd, J=14.1, 4.7 Hz, 1 H), 5.00 (dd, J=10.4, 4.7 Hz, 1 H), 7.56 (d, J=8.4 Hz, 2 H), 7.76 (d, J=8.4 Hz, 2 H), 12.09 (s, 1 H); MS (ES) m/z: 368.9 (M++H); HRMS Calcd. for C15H16N2O5S2(M++H): 368.0501. Found: 368.0481. Anal. Calcd. for C15H16N2O5S2: C, 48.90; H, 4.38; N, 7.60. Found: C,48.63; H, 4.35; N, 7.38.

Sources & evidence

ORD record
ord-46c7e8855608469dbe140160c9f6a427
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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