Tetrahydrofuran → HCID 86744822, compound

HRID 1493280Notes

Reaction equation

ClCCC[N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=23)[S:6]1(=[O:18])=[O:17].[OH:19][C:20]1([C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+].O1C[CH2:41][CH2:40][CH2:39]1>CN(C)C=O>[Br:32][C:29]1[CH:30]=[CH:31][C:26]([C:20]2([OH:19])[CH2:21][CH2:22][N:23]([CH2:39][CH2:40][CH2:41][C:10]3[C:9]4[NH:5][S:6](=[O:17])(=[O:18])[C:7]5[C:8]=4[C:13]([CH:14]=[CH:15][CH:16]=5)=[CH:12][CH:11]=3)[CH2:24][CH2:25]2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The experiment is carried out as in Exampe 1, starting with 2-(3-chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (2.8 g), 4-hydroxy-4-(4-bromophenyl)piperidine (2.4 g) and sodium bicarbonate (0.94 g) in a mixture of dimethylformamide (80 cc) and tetrahydrofuran (50 cc). The mixture is heated for 5 hours to a temperature of about 100° C. then cooled to a temperature of about 20° C. Stirring is maintained for 15 hours at this temperature. After purification by flash-chromatography on a silica column, under a current of argon (0.5-1.5 bar) with a mixture of dichloromethane and methanol (95-5 vol) as eluant, and recrystallization from boiling ethyl acetate (50 cc), 2-(3-[4-(4-bromophenyl)-4-hydroxypiperidino]propylnaphtho[1,8-cd]isothiazole 1,1-dioxide (1.5 g) is obtained in the form of hydrochloride, of m.p. 110 C.

Workup

temperaturethen cooled to a temperature of about 20° C
temperatureis maintained for 15 hours at this temperature
customAfter purification by flash-chromatography on a silica column
additionunder a current of argon (0.5-1.5 bar) with a mixture of dichloromethane and methanol (95-5 vol) as eluant
customrecrystallization

Sources & evidence

ORD record: ord-83eb0bbf210f4e4c96d57564004bd93d
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021420

Reaction notes

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