반응 #62008

반응 방정식

product

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

4-Phenyl-piperidin-4-ol

sodium triacetoxyborohydride

DCM

sodium hydroxide

→

ammonia DCM

수율 1.0%

title compound

4-Phenyl-1-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperidin-4-ol

용매

acetic acid

반응 조건

후처리

1. 1
   추출extracted with DCM (3×10 mL)
2. 2
   건조The combined organic phases were dried (sodium sulfate)
3. 3
   기타evaporated

실험 절차

A solution of the product of Example 9 (210 mg), 4-Phenyl-piperidin-4-ol (150 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (225 mg). 1H NMR (400 MHz, CDCl3): 7.54-7.49 (m, 2H), 7.37-7.33 (m, 2H), 7.28-7.23 (m, 3H), 6.88-6.84 (m, 2H), 3.99 (t, J=6.3 Hz, 2H), 3.51 (s, 2H), 2.78 (m, 2H), 2.50-2.36 (m, 8H), 2.15 (m, 2H), 1.97 (m, 2H), 1.73 (m, 2H), 1.63-1.55 (m, 4H), 1.47-1.40 (m, 2H).

출처