Triethylamine → HCID 14580031, compound

HRID 1087480Notes

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].C(N(CC)CC)C.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C1(C)C=CC=CC=1>[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:33][CH2:34][N:35]([CH2:2][CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=34)[S:6]2(=[O:18])=[O:17])[CH2:36][CH2:37]1

Participants

Conditions

Temperature: 20 °C

Procedure

The experiment is carried out as in Example 1, starting with 2-(3-chloropropyl)naphtho[1,8-cd]-isothiazole 1,1-dioxide (8.5 g), triethylamine (4.2 cc) and 1-(2-pyridyl)piperazine (4.7 cc) in toluene (8cc). The mixture is heated for 2 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 ethyl acetate as eluant, and recrystallization from boiling acetonitrile (30 cc), 2-{3-[4-(2-pyridyl)-1-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (4.2 g) is obtained, m.p. 101° C.

Workup

temperatureThe mixture is heated for 2 hours
customAfter purification by flash-chromatography on a silica column
customunder a current of argon at medium pressure (0.5-1.5 bar) with ethyl acetate as eluant, and recrystallization

Sources & evidence

ORD record: ord-20fa9663d07c4462a38d74c7f690fc38
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05036075

Reaction notes

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