Reaktion #41278

Reaktionsgleichung

Bromoethane

compound 12a

{3-[(Anthracen-9-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester

K2CO3

→

12b

Ausbeute 80.0%

[3-(Anthracen-9-ylmethyl-ethyl-amino)-propyl]-carbamic acid tert-butyl ester

Ausbeute 80.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter the confirmation of the disappearance of the 12a by TLC, the solution was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (20 mL)
3. 3
   Waschenwashed three times with aqueous sodium carbonate
4. 4
   SonstigeThe organic layer was separated
5. 5
   Trocknendried with anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under vacuum

Vorschrift

Bromoethane (489 mg, 4.48 mmol) was dissolved in anhydrous acetonitrile and was added to the stirring mixture of compound 12a (545 mg, 1.5 mmol) and anhydrous K2CO3 (620 mg, 4.48 mmol). The mixture was then stirred at 75° C. under a N2 atmosphere overnight. After the confirmation of the disappearance of the 12a 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 12b as a light yellow oil. Yield 80%; Rf=0.35 (3% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.39 (d, 2H), 8.30 (s, 1H), 7.90 (d, 2H), 7.40 (m, 4H), 4.54 (br t, 1H), 4.37 (s, 2H), 2.74 (q, 2H), 2.60 (q, 2H), 2.39 (t, 2H), 1.44 (q, 2H), 1.31 (m, 9H), 1.12 (t, 3H); 13C NMR (CDCl3) δ 155.7, 131.3 (2C), 131.2 (2C), 130.4 (2C), 129.0 (2C), 127.5 (2C), 125.7 (2C), 124.8 (2C), 78.3, 50.6, 50.5, 47.7, 39.1, 28.6 (3C), 26.6, 11.8. HRMS (FAB) m/z calcd. for C25H32N2O2 (M+H)+ 393.2537; found 393.2523.

Quelle