Pentane → HCID 10132558, compound

Temperature

-5 °C

A solution of benzo[b]furan (612 mg, 5.12 mmol) in dry THF (40 ml) was cooled to −8° C. under a stream of argon. Thereafter, tert-Butyllithium (6.22 mmol, 4.14 ml of a 1.5 molar pentane solution) was added dropwise such that a reaction temperature of −5° C. was not exceeded during the addition. When the addition had ended the reaction mixture was stirred for two hours at −5° C. Thereafter, a solution of 4-benzyl-4-dimethylaminocyclohexanone (1.20 g, 5.18 mmol) in dry THF (10 ml) was added dropwise at 0° C. The mixture was stirred for one hour at 0° C. and then for four days 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 30 ml methylene chloride each time. 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=8:2). 380 mg 1-benzofuran-2-yl-4-benzyl-4-dimethylaminocyclohexanol with a melting point of 121-124° C. were obtained.

1. additionwas not exceeded during the addition
2. additionWhen the addition
3. stirringThe mixture was stirred for one hour at 0° C.
4. waitfor four days 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 30 ml methylene chloride each time
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-959c111e8ed34a97a9f5abf3d7440f06

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678834B2