Hydrochloric Acid → HCID 54525242, compound

Temperature

115 °C

In a 75 ml pressure reactor equipped with a magnetic stirrer, 4.16 g racemic trans-2-(benzylidenamino)-cyclohexyl methanesulfonic acid ester (14.7 mmol) obtained according to (d) were dissolved in 20 ml of acetonitrile and the white-yellow solution was mixed with 4.50 ml of allylamine (59.2 mmol). The closed system was heated during 20 h at 115° C., then cooled to 0° C. and the viscous solution concentrated. 20 ml of toluene and 22 ml 4N HCl (88.2 mmol) were added and the two-phase mixture was vigorously stirred during 2 h and the two phases were separated. The aqueous phase was extracted with 20 ml of toluene. To the aqueous phase, 7.9 ml 50% aqueous potassium hydroxide solution (102.9 mmol) were added with vigorous stirring and the mixture was extracted with 20 ml of toluene. The brown organic phase was dried with 10 g sodium sulfate, filtered and washed with 10 ml of toluene. The solvent was removed in a rotary evaporator (45° C./60-10 mbar). The product was purified by high-vacuum distillation on a Diekmann evaporator at 34° C.-36° C./0.25-0.3 mbar to obtain 0.95 g of racemic trans-2-(allylamino)-cyclohexylamine as white viscous liquid was thus obtained.

1. temperaturecooled to 0° C.
2. concentrationthe viscous solution concentrated
3. customthe two phases were separated
4. extractionThe aqueous phase was extracted with 20 ml of toluene
5. stirringwith vigorous stirring
6. extractionthe mixture was extracted with 20 ml of toluene
7. dry with materialThe brown organic phase was dried with 10 g sodium sulfate
8. filtrationfiltered
9. washwashed with 10 ml of toluene
10. customThe solvent was removed in a rotary evaporator (45° C./60-10 mbar)
11. distillationThe product was purified by high-vacuum distillation on a Diekmann evaporator at 34° C.-36° C./0.25-0.3 mbar

ORD record

ord-158d6bf12231414fa124aa437d15a6f0

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437171B1