反应 #41278

反应方程式

Bromoethane

compound 12a

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

K2CO3

→

12b

收率 80.0%

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

收率 80.0%

溶剂

acetonitrile

反应条件

后处理

1. 1
   浓缩After 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
   洗涤washed three times with aqueous sodium carbonate
4. 4
   其他The organic layer was separated
5. 5
   干燥dried with anhydrous Na2SO4
6. 6
   过滤filtered
7. 7
   浓缩concentrated under vacuum

实验过程

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.

来源