Sodium Bicarbonate → 2-{2-[4-((5-Fluoro-3-indolyl)methyl)piperidino]ethyl}-3-phenyl-1,2-benzisothiazole 1,1-dioxide

HRID 1196606Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]2[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=2[S:5]1(=[O:20])=[O:19].[F:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[C:25]2[CH2:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1>[F:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[C:25]2[CH2:31][CH:32]1[CH2:37][CH2:36][N:35]([CH2:2][CH2:3][N:4]2[CH:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:7]3[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=3[S:5]2(=[O:20])=[O:19])[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 20 °C

Procedure

The procedure is as in Example 1, starting with 2-(2-chloroethyl)-3-phenyl-1,2-benzisothiazole 1,1-dioxide (2.85 g), 4-[(5-fluoro-3-indolyl)methyl]-piperidine (2.15 g) and sodium bicarbonate (2.3 g) in a mixture of dimethylformamide (30 cc) and tetrahydrofuran (20 cc). The mixture is heated to boiling for 48 hours and then cooled to a temperature in the region of 20° C. After purification by flash chromatography on a silica column under a stream of nitrogen at moderate pressure (0.5-1.5 bar) with a mixture of ethyl acetate and cyclohexane (80:20 by volume) as eluent, 2-{2-[4-((5-fluoro-3-indolyl)methyl)piperidino]ethyl}-3-phenyl-1,2-benzisothiazole 1,1-dioxide (2.6 g) is obtained, and is converted to a hydrochloride, m.p. 175° C.

Workup

temperatureThe mixture is heated
customAfter purification by flash chromatography on a silica column under a stream of nitrogen at moderate pressure (0.5-1.5 bar)
additionwith a mixture of ethyl acetate and cyclohexane (80:20 by volume) as eluent

Sources & evidence

ORD record: ord-35f36239b7b048e8ade53a47194176a8
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05114949

Reaction notes

Loading…