Potassium Carbonate → HCID 19830855, compound

HRID 1493264Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:19][CH2:20][CH2:21]Cl)[S:10](=[O:18])(=[O:17])[C:11]3[C:12]=2[C:13]=1[CH:14]=[CH:15][CH:16]=3)(=[O:3])[CH3:2].[C:23]1([C:29]2[CH2:30][CH2:31][NH:32][CH2:33][CH:34]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:19][CH2:20][CH2:21][N:32]3[CH2:31][CH:30]=[C:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:34][CH2:33]3)[S:10](=[O:18])(=[O:17])[C:11]3[C:12]=2[C:13]=1[CH:14]=[CH:15][CH:16]=3)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

5-Acetylamino-2-(3-chloropropyl)naphto[1,8-cd]isothiazole 1,1-dioxide (0.8 g), 4-phenyl-1,2,3,6-tetrahydropyridine (0.4 g), potassium carbonate (4 g) and acetonitrile (25 cc) are heated at boiling point for 20 hours. The reaction mixture is cooled to a temperature of about 20° C. The solution is filtered and then concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is purified by chromatography on a silica column with a mixture of ethyl acetate and methylene chloride (70-30 vol) as eluant, then recrystallized from boiling ethanol (20 cc). 5Acetylamino-2-[3-(4-phenyl 1,2,3,6-tetrahydro-1-pyridyl)-propyl]naphtho[1,8-cd]isothiazole 1,1-dioxide (0.35 g) is obtained, m.p. 178° C.

Workup

customfor 20 hours
filtrationThe solution is filtered
concentrationconcentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
customThe residue is purified by chromatography on a silica column with a mixture of ethyl acetate and methylene chloride (70-30 vol) as eluant
customrecrystallized

Sources & evidence

ORD record: ord-898407cf227f46dab571852d1dc393f3
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021420

Reaction notes

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