Hydrochloric Acid → HCID 86745691, compound

Temperature

0 °C

A flask containing 2-methylthio-trans-3a,4,5,6,7,7a-hexahydro-1H-benzimidazole hydroiodide (4.39 g, 1.47×10-2 mole) and 2,2-diphenylethylamine (2.90 g, 1.47×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 155°-165° C. for 40 minutes. The resulting yellow glass was dissolved in methanol. The methanol was evaporated at reduced pressure and isopropanol was added periodically during the course of the evaporation. When the solution had been concentrated to ca. 20 ml, it was set aside to cool. After 4 days the solution had deposited a solid which was collected by filtration. This guanidine hydroiodide was dissolved in a two phase mixture of 5 molar aqueous NaOH (100 ml) and CH2Cl2 (100 ml). After stirring overnight the CH2Cl2 layer was separated. The aqueous alkaline layer was extracted with CH2Cl2 (2×). The CH2Cl2 layers were combined, washed with H2O (2×), washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving a colorless foam which was dissolved in methanol (50 ml). The solution was cooled to 0° C. before being treated with a methanolic solution of HCl. The methanol was evaporated at reduced pressure leaving a foam. The foam was dissolved in methanol (10-15 ml) and 2-butanone was added. The solution was then concentrated on the steam bath. When the temperature of the solution reached ca. 75° C. a solid began to precipitate and the evaporation was stopped. After standing 2 hours the precipitate was collected by filtration affording a solid. This material was recrystallized from methanol/2-butanone affording 2-2,2-diphenylethylamino)-trans-3a,4,5,6,7,7a-hexahydro-1H-benzimidazole hydrochloride as a colorless solid: 3.86 g (74%), m.p. 216°-218° C.

1. customwas immersed in an oil bath
2. customhad been preheated to ca. 155° C
3. customThe methanol was evaporated at reduced pressure and isopropanol
4. additionwas added periodically during the course of the evaporation
5. concentrationWhen the solution had been concentrated to ca. 20 ml, it
6. temperatureto cool
7. waitAfter 4 days the solution had deposited
8. filtrationa solid which was collected by filtration
9. dissolutionThis guanidine hydroiodide was dissolved in a two phase mixture of 5 molar aqueous NaOH (100 ml) and CH2Cl2 (100 ml)
10. stirringAfter stirring overnight the CH2Cl2 layer
11. customwas separated
12. extractionThe aqueous alkaline layer was extracted with CH2Cl2 (2×)
13. washwashed with H2O (2×)
14. washwashed with saturated aqueous NaCl
15. dry with materialdried over anhydrous Na2SO4
16. customThe drying agent was removed by filtration
17. customthe filtrate was evaporated at reduced pressure
18. customleaving a colorless foam which
19. customThe methanol was evaporated at reduced pressure
20. customleaving a foam
21. concentrationThe solution was then concentrated on the steam bath
22. customreached ca. 75° C.
23. customto precipitate
24. customthe evaporation
25. waitAfter standing 2 hours
26. filtrationthe precipitate was collected by filtration
27. customaffording a solid
28. customThis material was recrystallized from methanol/2-butanone

ORD record

ord-cbd4b5dc0c3f4dfe859d9dc64ea3d3f8

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05106845