Benzothiazole → HCID 18436278, compound

Temperature

-80 °C

A solution of benzothiazole (622 mg, 4.60 mmol) in dry THF (30 ml) was cooled to −85° C. under a stream of argon. n-butyllithium (5.52 mmol, 3.45 ml of a 1.6 molar hexane solution) was added dropwise in such a way that a reaction temperature of −78° C. was not exceeded. Once all the substance had been added, the reaction mixture was stirred for 2 hours at −80° C. A solution of 4-dimethylamino-4-phenylcyclohexanone (1.00 g, 4.61 mmol) in dry THF (8 ml) was added dropwise at −80° C. The mixture was stirred for 30 minutes at −80° C. and then 3 days at ambient temperature. The reaction mixture was quenched with saturated ammonium chloride solution (30 ml), the organic phase was separated and the aqueous phase extracted four times with dichloromethane (30 ml). The combined organic phases were dried over sodium sulfate, filtered and the solvent removed under vacuum. Purification was carried out b y flash chromatography with cyclohexane/ethylacetate (V:V=7:3) over silica gel. 746 mg 1-benzothiazol-2-yl-4-dimethylamino-4-phenylcyclohexanol with a melting point of 155–157° C. were obtained.

1. additionOnce all the substance had been added
2. stirringThe mixture was stirred for 30 minutes at −80° C.
3. custom3 days
4. customat ambient temperature
5. customThe reaction mixture was quenched with saturated ammonium chloride solution (30 ml)
6. customthe organic phase was separated
7. extractionthe aqueous phase extracted four times with dichloromethane (30 ml)
8. dry with materialThe combined organic phases were dried over sodium sulfate
9. filtrationfiltered
10. customthe solvent removed under vacuum
11. customPurification

ORD record

ord-6d393abd80934673bf4e6ff0fdf9e700

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183436B2