1-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one → 1,1-dioxido-2-(4-(4-(3,4-dihydro-2-oxo-(1H)-quinolin-1-yl)-piperidin-1-yl)-butyl)-1,2-benzisothiazol-3(2H)-one

HRID 962721Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][C:8]2=[O:17])[CH2:3][CH2:2]1.Br[CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[S:24]1(=[O:34])=[O:33]>>[O:33]=[S:24]1(=[O:34])[C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[C:27](=[O:28])[N:23]1[CH2:22][CH2:21][CH2:20][CH2:19][N:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][C:8]2=[O:17])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 107281851-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one

HCID 107817741,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one

Product 1

HCID 190858281,1-dioxido-2-(4-(4-(3,4-dihydro-2-oxo-(1H)-quinolin-1-yl)-piperidin-1-yl)-butyl)-1,2-benzisothiazol-3(2H)-one

Procedure

From the hydrochloride salt of 3,4-dihydro-1-(4-piperidyl)-2(1H)-quinolinone prepared according to H. Ogawa et. al. J. Med. Chem. 1993, 36, 2011-2017, and 2-(4-bromobutyl)-1,1-dioxido-1,2-benzothiazol-3(2H)-one using the procedure described for Example 15, Step 5 there was obtained 1,1-dioxido-2-(4-(4-(3,4-dihydro-2-oxo-(1H)-quinolin-1-yl)-piperidin-1-yl)-butyl)-1,2-benzisothiazol-3(2H)-one as a white solid: 1H NMR (300 MHz, CDCl3) 8.07 (dd, J=6.5, 2.3 Hz, 1H), 7.92 (t, J=6.73 Hz, 1H), 7.84 (m, 2H), 7.21 (t, J=8.73 Hz, 2H), 7.19 (m, 1H), 6.99 (t, J=7.13 Hz, 1H), 4.35 (tt, J=12.2, 4.2 Hz, 1H), 3.83 (t, J=7.32 Hz, 2H), 3.04 (d, J=11.42 Hz, 2H), 2.81 (t, J=6.59 Hz, 2H), 2.61 (m, 3H), 2.43 (t, J=7.19 Hz, 2H), 2.09 (t, J=11.71 Hz, 2H), 1.88 (m, 2H), 1.69 (m, 5H).

Sources & evidence

ORD record: ord-8e0f9a8a8b444b10a8b79dbef18fe182
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05760054

Reaction notes

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