Pentane → HCID 9947106, compound

Temperature

0 °C

A solution of N-methylindole (1.50 mg, 3.81 mmol) in dry THF (20 ml) was cooled to −5° C. under a stream of argon. Thereafter, tert-butyllithium (4.19 mmol, 2.47 ml of a 1.7 molar pentane solution) was added dropwise such that a reaction temperature of 0° C. was not exceeded during the addition. When the addition had ended the reaction mixture was stirred for a further two hours at 0° C. A solution of 4-benzyl-4-dimethylaminocyclohexanone (3.88 mg, 3.81 mmol) in dry THF (7 ml) was then added dropwise at 0° C. The mixture was stirred for 15 minutes at 0° C. and then for four hours at room temperature. The reaction mixture was quenched with saturated ammonium chloride solution (20 ml), the organic phase was separated and the aqueous phase was extracted four times with methylene chloride (20 ml). The combined organic phases were dried over sodium sulfate and filtered and the solvent was removed in vacuo. Purification was carried out by means of flash chromatography over silica gel with cyclohexane/ethyl acetate (v/v=4:1). 456 mg 4-benzyl-4-dimethylamino-1-(1-methyl-1H-indol-2-yl) cyclohexanol with a melting point of 105-107° C. were obtained.

1. additionwas not exceeded during the addition
2. additionWhen the addition
3. stirringThe mixture was stirred for 15 minutes at 0° C.
4. waitfor four hours at room temperature
5. customThe reaction mixture was quenched with saturated ammonium chloride solution (20 ml)
6. customthe organic phase was separated
7. extractionthe aqueous phase was extracted four times with methylene chloride (20 ml)
8. dry with materialThe combined organic phases were dried over sodium sulfate
9. filtrationfiltered
10. customthe solvent was removed in vacuo
11. customPurification

ORD record

ord-6ee6845e7c3340bd834b475edf74356a

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678834B2