Hydrochloric Acid → HCID 58959759, compound

Temperature

80 °C

To 39.6 ml of a 3M solution ethylmagnesium bromide in ether was added 100 mL of dry tetrahydrofuran under an atmosphere of nitrogen. Then 16.7 mL of diisopropylamine was added dropwise. The reaction mixture was then heated to 80° C. for 1 h. After cooling to room temperature, the mixture was treated with a solution of 6.19 g of 1-(2,4-dichlorophenyl)piperidine-2-thione in 50 mL of dry tetrahydrofuran, heated to 80° C. for 30 min, and cooled again to room temperature. Then the mixture was treated dropwise with 10.0 mL of dimethylcarbonate and heated to 80° C. for 26 h. After cooling to room temperature, 100 g of ice was added along with 150 mL of 1.2M HCl. The mixture was extracted three times with 100 mL portions of dichloromethane. The combined organic extracts were washed with 100 mL of brine, dried over magnesium sulfate, concentrated, and then kept under high vacuum at 50° C. to remove the higher boiling volatile materials. The residue was purified by flash silica gel chromatography using 7% acetone/hexane as solvent yielding 5.25 g of 1-(2,4-dichlorophenyl)-2-methylsulfanyl-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester as a yellow solid, mp 83-86° C.

1. temperatureAfter cooling to room temperature
2. temperatureheated to 80° C. for 30 min
3. temperaturecooled again to room temperature
4. temperatureheated to 80° C. for 26 h
5. temperatureAfter cooling to room temperature
6. extractionThe mixture was extracted three times with 100 mL portions of dichloromethane
7. washThe combined organic extracts were washed with 100 mL of brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated
10. customkept under high vacuum at 50° C.
11. customto remove the
12. customThe residue was purified by flash silica gel chromatography

ORD record

ord-39fe10e9197b4f668ac12792a95aa7b5

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07268146B2