Water → 2-[1-(6-Chlorobenzothiazole-2-yl)-4-ethyl piperidine-4-yl]ethanol

HRID 420581Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][C:11]1([CH2:27][CH3:28])[CH2:16][CH2:15][N:14]([C:17]2[S:18][C:19]3[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:13][CH2:12]1.O.[OH-].[Na+]>O1CCCC1>[Cl:26][C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[C:17]([N:14]3[CH2:15][CH2:16][C:11]([CH2:10][CH2:9][OH:8])([CH2:27][CH3:28])[CH2:12][CH2:13]3)[S:18][C:19]=2[CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (202 mg) was suspended in tetrahydrofuran (10 mL). A solution of [1-(6-chlorobenzothiazole-2-yl)-4-ethyl piperidine-4-yl]acetic acid methyl ester (940 mg) in tetrahydrofuran (10 mL) was added thereto at 0° C. After stirring at 0° C. for 1 hour, to the reaction solution were sequentially added water (0.2 mL), 10% sodium hydroxide (0.2 mL) and water (0.6 mL). The insoluble material was filtrated and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (790 mg). Yield: 91%.

Workup

customat 0° C
filtrationThe insoluble material was filtrated
extractionthe filtrate was extracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulphate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record: ord-8082b46304cb4dde8d8dcbe6c159b346
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097610B2

Reaction notes

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