Реакция #61981

Уравнение реакции

product

4-(3-Piperidin-1-yl-propoxy)-benzaldehyde

piperidin-4-yl-pyridin-2-yl-(2-pyrrolidin-1-yl-ethyl)-amine

sodium triacetoxyborohydride

DCM

sodium hydroxide

→

ammonia DCM

Выход 1.0%

title compound

{1-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-piperidin-4-yl}-pyridin-2-yl-(2-pyrrolidin-1-yl-ethyl)-amine

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   Экстракцияextracted with DCM (3×3 mL)
2. 2
   СушкаThe combined organic phases were dried (sodium sulfate)
3. 3
   Другоеevaporated

Методика

A solution of the product of Example 9 (30 mg), piperidin-4-yl-pyridin-2-yl-(2-pyrrolidin-1-yl-ethyl)-amine (29.8 mg), and acetic acid (0.015 mL) in DCM (1 mL) was treated with sodium triacetoxyborohydride (38 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (1 mL) and extracted with DCM (3×3 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-10% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (26 mg). 1H NMR (400 MHz, CDCl3): 8.12 (m, 1H), 7.39 (m, 1H), 7.21 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 6.53-6.47 (m, 2H), 4.44 (m, 1H), 3.99 (t, J=6.3 Hz, 2H), 3.51-3.47 (m, 2H), 3.46 (s, 2H), 2.95 (m, 2H), 2.62 (m, 6H), 2.49 (m, 2H), 2.42 (m, 4H), 2.12 (m, 2H), 1.98 (m, 2H), 1.84-1.78 (m, 5H), 1.75 (m, 1H), 1.68 (m, 2H), 1.63-1.57 (m, 4H), 1.44 (m, 2H).

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