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

HRID 1590315Notes

Reaction equation

HRID 1590315 reaction equation
[CH2:1]1[CH:5]2[CH2:6][C:7](=O)[CH:3]([CH2:4]2)[CH2:2]1.C(N(CC)CC)C.[NH2:16][C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=1[C:23]#[N:24]>C(Cl)Cl>[NH2:24][C:23]1[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C:17]=2[N:16]=[C:7]2[C:6]=1[CH:5]1[CH2:4][CH:3]2[CH2:2][CH2:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 2901752-Aminocyclohex-1-ene-1-carbonitrile

Product 1

HCID 143728299-Amino-1,2,3,4,5,6,7,8-octahydro-1,4-methanoacridineYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

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

Workup

  1. additionwas added
  2. customThe reaction mixture was then quenched with 12% aqueous NaCH (60 ml)
  3. stirringwas stirred vigorously with methylene chloride (60 ml)
  4. filtrationThe reaction mixture was then filtered through a 2" pad of diatomaceous earth (Celite (trademark))
  5. customThe organic phase was separated
  6. washwashed with water (2×50 ml)
  7. dry with materialdried (anhydrous MgSO4)
  8. customMethylene chloride was then removed under reduced pressure
  9. customto afford an oil which
  10. customwas triturated with pentane

Sources & evidence

ORD record
ord-3b7f23431bac4cc3ab8bba860835ee41
Source dataset
uspto-grants-1993_04
Patent number
US05202440

Reaction notes

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