Reaction #1677497

Reaction equation

norcamphor

triethylamine

2-amino-1-cyano-1-cyclohexene

→

title compound

Yield 13.0%

9-Amino-1,2,3,4,5,6,7,8-octahydro-1,4-methanoacridine

Yield 13.0%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe reaction mixture was then quenched with 12% aqueous NaCH (60 ml)
3. 3
   workup.STIRRINGwas stirred vigorously with methylene chloride (60 ml)
4. 4
   FiltrationThe reaction mixture was then filtered through a 2" pad of diatomaceous earth (Celite (trademark))
5. 5
   OtherThe organic phase was separated
6. 6
   Washwashed with water (2×50 ml)
7. 7
   Dryingdried (anhydrous MgSO4)
8. 8
   OtherMethylene chloride was then removed under reduced pressure
9. 9
   Otherto afford an oil which
10. 10
    Otherwas triturated with pentane

Procedure

To a stirred solution of norcamphor (0.9 g, 8.2 mmole) in methylene chloride (8.0 ml) at -20° C., a mixture of triethylamine (1.7 g, 16.4 mmole) and 2-amino-1-cyano-1-cyclohexene (1.0 g, 8.2 mmole) in methylene chloride (24 ml) was added and the resulting mixture was stirred at 25° C. for 15 hours. The reaction mixture was then quenched with 12% aqueous NaCH (60 ml) and was stirred vigorously with methylene chloride (60 ml). The reaction mixture was then filtered through a 2" pad of diatomaceous earth (Celite (trademark)). The organic phase was separated, washed with water (2×50 ml) and then dried (anhydrous MgSO4). Methylene chloride was then removed under reduced pressure to afford an oil which was triturated with pentane to give the title compound as a off-white solid (225 mg, 13%, m.p. 131°-133° C.). 1H-NMR (CDCl3, 300 MHz, δ): 2H, m, 1.15-2.38 ppm; 1H, d, 1.5 ppm; 7H, m, 165-2.0 ppm; 2H, bs, 2.4 ppm; 2H, bd, 2.8 ppm; 2H, bd 3.3 ppm; 2H, s, 3.95 ppm. HRMS: Calculated--214.3096; Found--214.1466. TLC: (90:10:1-methylene chloride: methanol:28% aqueous ammonia) Rf =0.25

Source