Reacción #5445

Ecuación de reacción

product

8-Methoxy-2-(2-aminoethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

p-fluorobenzoyl chloride

→

desired product

8-Methoxy-2-(2-(4-fluorobenzamido)ethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride

Disolventes

triethyl amine

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was quenched in 5% NaHCO3
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   SecadoThe organic extracts were dried (Na2SO4)
4. 4
   Otroevaporated
5. 5
   workup.DISSOLUTIONthe product was dissolved in ether
6. 6
   workup.ADDITIONtreated with ethereal HCl
7. 7
   Otroevaporated to dryness
8. 8
   OtroThe resulting product was recrystallized from ethyl acetate and ether

Procedimiento

The product from Example 17 (0.95 g) was dissolved in 50 ml methylene chloride and 1.5 ml triethyl amine. The solution was cooled to -20° C. and 0.59 ml p-fluorobenzoyl chloride was added. After 30 min, the reaction was quenched in 5% NaHCO3 and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), evaporated, and the product was dissolved in ether and treated with ethereal HCl and then evaporated to dryness. The resulting product was recrystallized from ethyl acetate and ether to yield 0.772 g of the desired product as a white solid, mp: 197°-8° C. NMR (d6DMSO) δ2.60-3.10 (m, 3H), 3.00-3.50 (m, 4H), 3.59 (m, 2H), 3.78 (s, 3H), 3.82-4.22 (m, 3H), 6.83 (d, 1H), 6.87 (d, 1H), 7.23 (t, 1H), 7.34 (m, 2 H), 8.00 (m, 2H).

Fuente