3-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride → HCID 21963398, compound

HRID 2211929Notes

Reaction equation

HRID 2211929 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:6]([CH3:16])=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:4].Cl.[N:18]1([C:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[S:26][N:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>>[S:26]1[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:24]([N:18]2[CH2:19][CH2:20][N:21]([CH2:2][C:3]([C:5]3[C:6]([CH3:16])=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[C:8]([CH3:11])=[CH:9][CH:10]=3)=[O:4])[CH2:22][CH2:23]2)=[N:25]1

Participants

3

Reactant 2

HCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21963188HCID 21963188, compound

Product 1

HCID 21963398HCID 21963398, compoundYield 65%

Procedure

Starting with N-[3-(2-chloro-acetyl)-2,6-dimethyl-phenyl]-acetamide (0.250 g, 1.04 mmol), and 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (0.290 g, 1.15 mmol) and following the procedure as outlined in Example 517, N-{3-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-acetyl]-2,6-dimethyl-phenyl}-acetamide (0.285 g, 0.67 mmol) was obtained as its hydrochloride salt from treatment with dioxane/HCl(gas). Yield=65%. 100% purity at 254 nM. 1H NMR (400 MHz, DMSO-d6) δ 9.29 (s, 2H), 8.00 (d, J=8.04 Hz, 2H), 7.55–7.47 (m, 2H), 7.38 (t, J=8.04 Hz, 1H), 7.14 (t, J=8.04 Hz, 1H), 3.76 (s, 2H), 4.13–3.99 (m, 2H), 3.42–3.36 (m, 4H), 3.28 (s, H2O), 2.45 (p, DMSO), 2.14–2.11 (m, 6H), 2.01 (s, 3H).

Sources & evidence

ORD record
ord-5889317b08b44c02831669d8de461aff
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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