Hydrochloric Acid → 3-(3,4-Dichloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene

To a stirred solution of 3-(3,4-dichlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol (50 g, 0.17 mol) in glacial acetic acid (160 mL) at room temperature was added concentrated hydrochloric acid (50 mL). The reaction mixture was heated at reflux. The starting material was consumed after 20 minutes and the reaction mixture was poured into approximately 1.5 L of crushed ice. The resulting aqueous solution was added concentrated NH4OH (approximately 325 mL) to pH=9-10 resulting in precipitation of a sticky solid. The mixture was decanted and the reminiscence was triturated in water (1.5 L) resulting in a crystalline crude product. The crude product was washed a last time with water (300 mL) and was dried in a fume hood yielding the title compound as an off-white solid, m.p. 44-52° C.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux
3. customThe starting material was consumed after 20 minutes
4. additionthe reaction mixture was poured into approximately 1.5 L of crushed ice
5. additionThe resulting aqueous solution was added concentrated NH4OH (approximately 325 mL) to pH=9-10
6. customresulting in precipitation of a sticky solid
7. customThe mixture was decanted
8. customthe reminiscence was triturated in water (1.5 L)
9. customresulting in a crystalline crude product
10. washThe crude product was washed a last time with water (300 mL)
11. customwas dried in a fume hood

ORD record

ord-0b712d8bf4e64a52a1acb27d62c3d47a

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06100275