Reaction #62002

Reaction equation

triphenylphosphine

DCM

product

4-Piperidin-1-ylmethyl-phenol

2-Diethylamino-ethanol

di-tert-butylazodicarboxylate

→

ammonia DCM

Yield 3.0%

title compound

Diethyl-[2-(4-piperidin-1-ylmethyl-phenoxy)-ethyl]-amine

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), 2-Diethylamino-ethanol (0.12 mL), 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 (3% 2 M methanolic ammonia/DCM) gave the title compound as a pale yellow oil (37 mg). 1H NMR (400 MHz, CDCl3): 7.20 (d, J=8.8 Hz, 2H), 6.84 (d, J=8.6 Hz, 2H), 4.03 (t, J=6.5 Hz, 2H), 3.40 (s, 2H), 2.87 (t, J=6.5 Hz, 2H), 2.63 (q, J=7.0 Hz, 4H), 2.35 (br s, 4H), 1.59-1.52 (m, 4H), 1.46-1.37 (m, 2H), 1.07 (t, J=7.1 Hz, 6H).

Source