Sodium sulfate decahydrate → 2-(2-piperidinoethyl)-8H-indeno[1,2-d]thiazole

HRID 356118Notes

Reaction equation

[N:1]1([C:7]([CH2:9][C:10]2[S:11][C:12]3[CH2:21][C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:13]=3[N:14]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[N:1]1([CH2:7][CH2:9][C:10]2[S:11][C:12]3[CH2:21][C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:13]=3[N:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 500 mg of 2-[(piperidinocarbonyl)methyl]-8H-indeno[1,2-d]thiazole in 10 ml of tetrahydrofuran was added to a suspension of 160 mg of lithium aluminum hydride in 10 ml of tetrahydrofuran at 0° C., followed by heating under reflux for 1.5 hours. The reaction mixture was cooled to 0° C. again, and sodium sulfate decahydrate was added. The resulting mixture was stirred at room temperature for 30 minutes. After the insoluble matter was removed by filtration, the solvent was evaporated. The resulting oily substance was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1), whereby 120 mg of 2-(2-piperidinoethyl)-8H-indeno[1,2-d]thiazole was obtained. Fumaric acid was added to the product in ethanol to cause crystallization, and the crystals were recrystallized to give a fumarate.

Workup

temperatureby heating
temperatureunder reflux for 1.5 hours
customAfter the insoluble matter was removed by filtration
customthe solvent was evaporated
customThe resulting oily substance was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1)

Sources & evidence

ORD record: ord-5a0bc6916ef741158a495d4306794aa3
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834499

Reaction notes

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