3-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride → HCID 21963407, compound

HRID 2211926Notes

Reaction equation

HRID 2211926 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][C:6]=1[NH:14][C:15](=[O: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]([CH:11]([CH3:13])[CH3:12])=[CH:7][C:6]=3[NH:14][C:15](=[O: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 21963281HCID 21963281, compound

Product 1

HCID 21963407HCID 21963407, compoundYield 73%

Procedure

Starting with N-[2-(2-chloro-acetyl)-5-isopropyl-phenyl]-acetamide (0.30 g, 1.182 mmol), and 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (0.302 g, 1.182 mmol) and following the procedure as outlined in Example 517, N-{2-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-acetyl]-5-isopropyl-phenyl}-acetamide (0.375 g, 0.859 mmol) was obtained as its hydrochloride salt from treatment with dioxane/HCl(gas). Yield=73%. 100% purity at 254 nM. 1H NMR (400 MHz, DMSO-d6) δ 10.71 (s, 1H), 10.36 (bs, 1H), 8.14 (d, J=8.24 Hz, 1H), 8.09 (d, J=8.24 Hz, 1H), 7.78–7.72 (m, 2H), 7.58 (t, J=7.56 Hz, 1H), 7.45 (t, J=7.56 Hz, 1H), 7.18 (d, J=8.24 Hz, 1H), 5.00 (s, 2H), 4.13–4.01 (m, 2H), 3.68–3.44 (m, 6H), 3.40 (s, H2O), 2.93 (heptet, J=6.95 Hz, 1H), 2.08 (s, 3H), 1.19 (d, J=6.95 Hz, 6H).

Sources & evidence

ORD record
ord-a201b1eba94c428fa1c8d06ab356c56c
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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