Sodium Iodide → 2-{2-[4-(4-Fluorobenzoyl)piperidino}ethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

HRID 1087488Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:6]([C:7]=23)[S:5]1(=[O:17])=[O:16].C(N(CC)CC)C.[F:25][C:26]1[CH:39]=[CH:38][C:29]([C:30]([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[O:31])=[CH:28][CH:27]=1.[I-].[Na+]>CN(C)C=O>[F:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([CH:32]2[CH2:37][CH2:36][N:35]([CH2:2][CH2:3][N:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[C:12]5[CH:13]=[CH:14][CH:15]=[C:6]([C:7]=45)[S:5]3(=[O:17])=[O:16])[CH2:34][CH2:33]2)=[O:31])=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 20 °C

Procedure

The experiment is carried out as in Example 1, starting with 2-(2-chloroethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (6.7 g), triethylamine (3.5 cc), 4-(4-fluorobenzoyl)piperidine (5.2 g) and sodium iodide (3.7 g) in dimethylformamide (100 cc). The mixture is heated for 6 hours at boiling point, then cooled to a temperature of about 20° C. After purification by flash-chromatography on a silica column, under current of argon at medium pressure (0.5-1.5 bar) with dichloromethane as eluant, and recrystallization from boiling acetonitrile (8 cc), 2-{2-[4-(4-fluorobenzoyl)piperidino}ethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (2.9 g) is obtained, m.p. 145° C.

Workup

temperatureThe mixture is heated for 6 hours
customAfter purification by flash-chromatography on a silica column
customunder current of argon at medium pressure (0.5-1.5 bar) with dichloromethane as eluant, and recrystallization

Sources & evidence

ORD record: ord-db2bed5810bc48afb434b4c36bb101ba
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05036075

Reaction notes

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