Reaction #61996

Reaction equation

triphenylphosphine

DCM

product

4-Piperidin-1-ylmethyl-phenol

3-(2-methyl-piperidin-1-yl)-propan-1-ol

di-tert-butylazodicarboxylate

→

ammonia DCM

Yield 2.5%

title compound

2-Methyl-1-[3-(4-piperidin-1-ylmethyl-phenoxy)-propyl]-piperidine

Conditions

Workup

1. 1
   Filtrationthe resulting mixture was filtered
2. 2
   Otherthe filtrate was evaporated

Procedure

A suspension of the product of Example 17 (176 mg), 3-(2-methyl-piperidin-1-yl)-propan-1-ol (145 mg), and polymer supported triphenylphosphine (613 mg; loading: 3 mmol/g) in DCM (5 mL) was treated with di-tert-butylazodicarboxylate (316 mg). After 2 h, the resulting mixture was filtered, and the filtrate was evaporated. Chromatography of the residue (2.5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (60 mg). 1H NMR (400 MHz, CDCl3): 7.20 (d, J=8.6 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 4.01-3.92 (m, 2H), 3.40 (s, 2H), 2.90-2.81 (m, 2H), 2.56-2.47 (m, 1H), 2.40-2.25 (m, 5H), 2.21-2.14 (m, 1H), 1.97-1.88 (m, 2H), 1.70-1.51 (m, 8H), 1.45-1.25 (m, 4H), 1.07 (d, J=6.2 Hz, 3H).

Source