Reacción #41273

Ecuación de reacción

mesylate

Methanesulfonic acid 3-(anthracen-9-ylmethyl-ethyl-amino)-propyl ester

3-amino-propanol

→

18

Rendimiento 65.0%

3-[3-(Anthracen-9-ylmethyl-ethyl-amino)-propylamino]-propan-1-ol

Rendimiento 65.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónAfter the confirmation of the disappearance of the mesylate by TLC, the solution was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (20 mL)
3. 3
   Lavadowashed three times with aqueous sodium carbonate
4. 4
   OtroThe organic layer was separated
5. 5
   Secadodried with anhydrous Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated under vacuum

Procedimiento

The mesylate 17 (384 mg, 1.04 mmol) and 3-amino-propanol (392 mg, 5.25 mmol) were dissolved in acetonitrile (20 mL). The mixture was then stirred at 75° C. under a N2 atmosphere overnight. After the confirmation of the disappearance of the mesylate by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 18 as a light yellow oil. Yield 65%; Rf=0.35 (1:6:83 NH4OH:MeOH:CH2Cl2); 1H NMR (CDCl3) δ 8.32 (d, 2H), 8.23 (s, 1H), 7.83 (d, 2H), 7.37 (m, 2H), 7.30 (m, 2H), 4.28 (s, 2H), 3.48 (t, 2H), 2.56 (q, 2H), 2.30 (t, 2H), 2.12 (t, 2H), 2.06 (t, 2H), 1.36 (q, 2H), 1.21 (q, 2H), 1.09 (t, 3H); 13C NMR (CDCl3) δ 131.3, 131.2, 130.5, 129.3, 129.0, 127.3, 125.5, 125.3, 124.8, 124.8, 63.8, 50.8, 50.5, 49.5, 48.3, 47.7, 30.5, 26.6, 11.7. HRMS (FAB) m/z calcd. for C23H30N2O (M+H)+ 351.2431; found 351.2430.

Fuente