Реакция #41278

Уравнение реакции

Bromoethane

compound 12a

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

K2CO3

→

12b

Выход 80.0%

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

Выход 80.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   КонцентрированиеAfter 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
   Промывкаwashed three times with aqueous sodium carbonate
4. 4
   ДругоеThe organic layer was separated
5. 5
   Сушкаdried with anhydrous Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated under vacuum

Методика

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.

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