Ethylamine → HCID 17875048, compound

Temperature

-16 °C

The product from Step C (1 g, 3 mmol) was dissolved in tetrahydrofuran (50 mL) containing triethylamine (1.7 mL, 12.0 mmol) and the solution was cooled to -16° C. Tosyl chloride (1.1 g, 6.0 mmol) was added and the mixture stirred for 18 h at room temperature after which time it was cooled to 0° C. and ethylamine (10 mL) was added. After heating at reflux for 1 h the solvent was evaporated and the residue dissolved in ethyl acetate (50 mL) and washed with 1N HCL (3×20 mL). The combined aqueous washes were basified (sodium bicarbonate) and extracted with ethyl acetate. The combined extracts were washed with saturated sodium bicarbonate solution (3×15 mL) and brine (3×15 mL), dried (MgSO4) and evaporated to give the desired free base (620 mg) as a syrup. This material was dissolved in ethanol (5 mL) and IN ethanolic HCL (5 mL) was added. This solution was then concentrated to dryness to give the desired product as a light yellow solid (400 mg): mp 243°-245° C.

1. temperaturewas cooled to 0° C.
2. temperatureAfter heating
3. temperatureat reflux for 1 h the solvent
4. customwas evaporated
5. dissolutionthe residue dissolved in ethyl acetate (50 mL)
6. washwashed with 1N HCL (3×20 mL)
7. extractionextracted with ethyl acetate
8. washThe combined extracts were washed with saturated sodium bicarbonate solution (3×15 mL) and brine (3×15 mL)
9. dry with materialdried (MgSO4)
10. customevaporated

ORD record

ord-0e16061764734d6ca7589782b0d8b483

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05240923