Dimethylformamide → 2-{3-[4-(4-Methylphenyl)-4-hydroxypiperidino]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide

HRID 1493274Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][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]([CH3:32])=[CH:28][CH:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+].CN(C)C=O>O1CCCC1>[CH3:32][C:29]1[CH:28]=[CH:27][C:26]([C:20]2([OH:19])[CH2:25][CH2:24][N:23]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]5[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=45)[S:6]3(=[O:18])=[O:17])[CH2:22][CH2:21]2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The experiment is carried out as in Example 1, starting with 2-(3-chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (2,8 g), 4-hydroxy-4-(4-methylphenyl)piperidine (2.1 g) and sodium bicarbonate (0.94 g) i mixture of dimethylformamide (60 cc) and tetrahydrofuran (50 cc). The mixture is heated for 5 hours at 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 at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and methanol (95-5 vol) as eluant, 2-{3-[4-(4-methylphenyl)-4-hydroxypiperidino ]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (1 g) is obtained, in the form of 1,1-dioxide (1 g) is obtained, in the form of the hydrochloride of m.p. 218° 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 at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and methanol (95-5 vol) as eluant

Sources & evidence

ORD record: ord-7ba983fc7df74a5f99b12cb1e3110a89
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021420

Reaction notes

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