Reaction #41281

Reaction equation

Bromoethane

compound 14a

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

K2CO3

→

14b

Yield 82.0%

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

Yield 82.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   ConcentrationAfter confirmation of the disappearance of 14a by TLC, the solution was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (20 mL)
3. 3
   Washwashed three times with aqueous sodium carbonate
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried with anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under vacuum

Procedure

Bromoethane (616 mg, 5.65 mmol) was dissolved in anhydrous acetonitrile and was added to the stirring mixture of compound 14a (500 mg, 1.9 mmol) and anhydrous K2CO3 (781 mg, 5.7 mmol). The mixture was then stirred overnight at 75° C. under a N2 atmosphere. After confirmation of the disappearance of 14a 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 14b as a light yellow oil. Yield 82%; Rf=0.35 (3% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.28 (m, 3H), 7.86 (d, 2H), 7.44 (m, 2H), 7.36 (m, 2H), 4.29 (s, 2H), 3.15 (t, 2H), 2.65 (q, 2H), 2.52 (t, 2H), 1.43 (q, 2H), 1.16 (t, 3H); 13C NMR (CDCl3) δ 131.2, 131.1, 129.3, 129.0, 127.6, 125.8, 124.8, 124.4, 63.4, 52.6, 50.5, 47.7, 28.1, 11.6. HRMS (FAB) m/z calcd. for C20H23NO (M+H)+ 294.1852; found 294.1859.

Source