Diisopropylamine → HCID 23311330, compound

To a solution of diisopropylamine (6.4 ml, 46 mmol) in anhydrous THF (50 ml) maintained at -70° under nitrogen was added n-BuLi/hexane (2.2M, 20 ml, 44 mmol). The solution was stirred at -70° for 15 minutes and brought to -30° C. A solution of alpha-(2-methoxyphenyl)-phenylacetonitrile (9.16 g, 40 mmol) in THF (50 ml) was added dropwise and the resultant solution was allowed to warm to 20° and stirred for 0.5 hour. Distilled 3-dimethylaminopropyl chloride (11.2 g, 92 mmol) was added dropwise and the mixture was refluxed 16 hours. The reaction mixture was cooled and quenched with H2O (5 ml), the volatiles were evaporated in vacuo and the residue was dissolved in dichloromethane (300 ml) and washed with H2O (3×100 ml) until the pH of the aqueous phase became 8. The organic solution was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was dissolved in diethyl ether (300 ml) and saturated with gaseous HCl. The crude precipitated salt (10.4 g, 84%) was collected and dried. Analytically pure material (5.2 g, 38%) was obtained by recrystallization from acetonitrile, m.p. 194.0°-195.5°.

1. custombrought to -30° C
2. temperatureto warm to 20°
3. stirringstirred for 0.5 hour
4. temperaturethe mixture was refluxed 16 hours
5. temperatureThe reaction mixture was cooled
6. customquenched with H2O (5 ml)
7. customthe volatiles were evaporated in vacuo
8. dissolutionthe residue was dissolved in dichloromethane (300 ml)
9. washwashed with H2O (3×100 ml) until the pH of the aqueous phase
10. dry with materialThe organic solution was dried over Na2SO4
11. filtrationfiltered
12. customevaporated in vacuo
13. dissolutionThe residue was dissolved in diethyl ether (300 ml) and saturated with gaseous HCl
14. customThe crude precipitated salt (10.4 g, 84%)
15. customwas collected
16. customdried

ORD record

ord-626b0b1249d241b8a2526f5bfe08c75d

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04602035