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

HRID 2211912Notes

Reaction equation

HRID 2211912 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:14])[C:11](=[O:13])[CH3:12])=[C:6]([CH3:15])[CH:5]=1.Cl.[N:17]1([C:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[S:25][N:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>>[S:25]1[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:23]([N:17]2[CH2:18][CH2:19][N:20]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([N:10]([CH3:14])[C:11](=[O:13])[CH3:12])=[C:6]([CH3:15])[CH:5]=3)[CH2:21][CH2:22]2)=[N:24]1

Participants

3

Reactant 2

HCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21963208N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-N-methyl-acetamide

Product 1

HCID 10476580N-{4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenyl}-N-methyl-acetamideYield 71%

Procedure

Starting with N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-N-methyl-acetamide (0.226 g, 1.00 mmol) and 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (0.384 g, 1.50 mmol), and following the procedure outlined in Example 501, N-{4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenyl}-N-methyl-acetamide was obtained as its hydrochloride salt (0.341 g, 0.41 mmol). Yield=71%;100% purity at 254 nm; LCMS (APCI): 409.2 [M+H]+, 1H NMR (400 MHz, DMSO-d6) δ 8.12 (d, J=7.51 Hz, 1H), 8.08 (d, J=7.51 Hz, 1H), 7.57 (t, J=7.51 Hz, 1H), 7.44 (t, J=7.51 Hz, 1H), 7.26 (s, 1H), 7.24–7.19 (m, 2H), 4.07 (d, J=13.23 Hz, 2H), 3.65 (d, J=13.23 Hz, 2H), 3.53 (apparent t, J=12.21 Hz, 2H), 3.44–3.22 (m, 4H), 3.19–3.07 (m, 2H), 3.00 (s, 3H), 2.14 (s, 3H), 1.60 (s, 3H); Anal. Calcd for C23H29N4O1S1Cl1: C, 60.88; H, 6.49; N, 12.35. Found: C, 60.48; H, 6.59; N, 11.98.

Sources & evidence

ORD record
ord-d985b29fd40040a99fba19beb69aa9bd
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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