Triethylamine → 2-[2-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)ethyl]naphtho[1,8-cd]isothiazole 1,1-dioxide

HRID 1087485Notes

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.[C:25]1([C:31]2[CH2:32][CH2:33][NH:34][CH2:35][CH:36]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[C:25]1([C:31]2[CH2:36][CH2:35][N:34]([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])[CH2:33][CH:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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 (6.5 g), triethylamine (3.4 cc) and 4-phenyl-1,2,3,6-tetrahydropyridine (3.9 g) in toluene (150 cc). The mixture is heated for 9 hours at boiling point, then cooled to a temperature of about 20° C. After purification by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with dichloromethane as eluant, and recrystallization from boiling acetonitrile (10 cc), 2-[2-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)ethyl]naphtho[1,8-cd]isothiazole 1,1-dioxide (2.5 g) is obtained, m.p. 106° C.

Workup

temperatureThe mixture is heated for 9 hours
customAfter purification by flash-chromatography on a silica column
customunder a current of argon at medium pressure (0.5-1.5 bar) with dichloromethane as eluant, and recrystallization

Sources & evidence

ORD record: ord-b7a36a6d3b894aa9a6340f9f9936b34b
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05036075

Reaction notes

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