3-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride → HCID 21963599, compound

HRID 2211927Notes

Reaction equation

HRID 2211927 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]=1[CH:15]([CH3:17])[CH3:16])=[O:4].Cl.[N:19]1([C:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[S:27][N:26]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[S:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:25]([N:19]2[CH2:20][CH2:21][N:22]([CH2:2][C:3]([C:5]3[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]=3[CH:15]([CH3:17])[CH3:16])=[O:4])[CH2:23][CH2:24]2)=[N:26]1

Participants

3

Reactant 2

HCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21963361HCID 21963361, compound

Product 1

HCID 21963599HCID 21963599, compoundYield 67%

Procedure

Starting with N-[4-(2-chloro-acetyl)-3-isopropyl-phenyl]-acetamide (0.876 g, 3.453 mmol), and 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (0.883 g, 3.453 mmol) and following the procedure as outlined in Example 517, N-{4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-acetyl]-3-isopropyl-phenyl}-acetamide (0.1.0 g, 2.302 mmol) was obtained as its hydrochloride salt from treatment with dioxane/HCl(gas). Yield=67%. 100% purity at 254 nM. 1H NMR (400 MHz, DMSO-d6) δ 10.44–10.29 (bm, 2H), 8.13 (d, J=8.49 Hz, 1H), 8.09 (d, J=8.49 Hz, 1H), 7.81 (d, J=9.12 Hz, 1H), 7.73–7.68 (m, 2H), 7.57 (t, J=7.49 Hz, 1H), 7.45 (t, J=7.49 Hz, 1H), 5.04 (s, 2H), 4.13–4.02 (m, 2H), 3.76–3.45 (m, 18H, H2O), 2.06 (s, 3H), 1.18 (d, J=6.85 Hz, 6H).

Sources & evidence

ORD record
ord-ffac0d3a545449beb8df5c568a3cd725
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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