4-(p-tolyl)piperidin-4-ol synthesis

6synthesis methods

Product Name:4-(p-tolyl)piperidin-4-ol
CAS Number:57988-60-0
Molecular formula:C12H17NO
Molecular Weight:191.27

1-Boc-4-hydroxy-4-(4-methylphenyl)piperidine

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57988-60-0
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Yield:57988-60-0 40%

Reaction Conditions:

with hydrogenchloride in ethyl acetate at 20;

Steps:

4-p-tolylpiperidin-4-ol(11f)

A solution of 10f (4.157g) and 3M HCl (10mL) in EtOAc (50mL) was stirred at room temperature. The reaction was neutralized with saturated NaOH, and the mixture was extracted with CH2Cl2 (3x30mL), washed with saturated NaCl solution and dried with Na2SO4. Filtration, evaporation in vacuo, and purification by flash chromatography (DCM: MeOH = 50:1-5:1) afforded 1.13g (40%) as a solid. Mp: 146-147 °C. ¹H NMR (300 MHz, CDCl3) δ 7.36 (d, J = 8.4 Hz, 2H), 7.14 (d, J = 8.4 Hz, 2H), 4.51 (m, 2H), 3.19-3.24 (m, 2H), 3.09 (m, 2H), 2.32 (s, 3H), 2.15-2.16 (m, 2H), 1.76-1.80 (m, 2H). LRESI-MS m/z: 192.0[M+H]⁺, 174.0[M+H-H20]⁺.

References:

Chen, Gang;Xia, Hongguang;Cai, Yu;Ma, Dawei;Yuan, Junying;Yuan, Chengye [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 1,p. 234 - 239] Location in patent:supporting information; experimental part