3-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride → N-{4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenyl}-N-ethyl-acetamide

HRID 2211915Notes

Reaction equation

HRID 2211915 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:14][CH3:15])[C:11](=[O:13])[CH3:12])=[C:6]([CH3:16])[CH:5]=1.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][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([N:10]([CH2:14][CH3:15])[C:11](=[O:13])[CH3:12])=[C:6]([CH3:16])[CH:5]=3)[CH2:22][CH2:23]2)=[N:25]1

Participants

3

Reactant 2

HCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21963286N-[4-(2-Chloro-ethyl)-2-methyl-phenyl]-N-ethyl-acetamide

Product 1

HCID 10025284N-{4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenyl}-N-ethyl-acetamideYield 70%

Procedure

Starting with N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-N-ethyl-acetamide (0.169 g, 0.706 mmol) and 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (0.271 g, 1.059 mmol) and following the procedure as outlined in Example 501, N-{4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenyl}-N-ethyl-acetamide (0.227 g, 0.494 mmol) was isolated in 100% purity @ 254 nm; LCMS (APCI): 423 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 11.37 (bs, 1H), 8.13 (d, J=7.84 Hz, 1H), 8.09 (d, J=7.84 Hz, 1H), 7.57 (t, J=7.12 Hz, 1H), 7.45 (t, J=7.12 Hz, 1H), 7.28 (s, 1H), 7.23–7.11 (m, 2H), 4.07 (bd, J=13.09 Hz, 2H), 3.88 (sextet, J=6.23 Hz, 1H), 3.66 (bd, J=11.22 Hz, 2H), 3.51 (bt, J=11.22 Hz, 2H), 3.45–3.37 (m, 2H), 3.35 (bs, DMSO-H2O), 3.33–3.22 (m, 3H), 2.14 (s, 3H), 1.58 (s, 3H), 0.97 (t, J=7.11 Hz, 3H).

Sources & evidence

ORD record
ord-795c602e0ce34aefb932330969e7a8db
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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