ChemicalBook CAS DataBase List 3-HYDROXY-3-PHENYL-PIPERIDINE

3-HYDROXY-3-PHENYL-PIPERIDINE synthesis

6synthesis methods

Product Name:3-HYDROXY-3-PHENYL-PIPERIDINE
CAS Number:23396-50-1
Molecular formula:C11H15NO
Molecular Weight:177.24

213923-81-0 Synthesis

213923-81-0
31 suppliers
$95.00/100mg

23396-50-1
44 suppliers
$21.00/100mg

Yield: 97%

Reaction Conditions:

with toluene-4-sulfonic acid in dichloromethane at 20; for 2 h;

Steps:

1.d (d)
3-Phenylpiperidin-3-ol (4)
(d)
3-Phenylpiperidin-3-ol (4)
Compound 3 (469 mg, 1.7 mmol) and p-toluenesulfonic acid monohydrate (675 mg, 3.5 mmol) were dissolved in dichloromethane (8.5 mL) and stirred for 2 h at room temperature. 3 N Potassium hydroxide (10 mL) was added to the reaction mixture, and extracted with dichloromethane (10 mL, 4 times).
The combined organic layers were washed with saturated brine (50 mL), and the aqueous layer was back extracted with dichloromethane (30 mL, 4 times).
The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford Compound 4 (291 mg, 97%) as pale yellow solid.
¹H NMR (300 MHz, CD₃OD) δ 7.53-7.46 (2H, m), 7.37-7.29 (2H, m), 7.26-7.18 (1H, m), 3.08-2.99 (1H, m), 2.93-2.85 (1H, m), 2.81-2.72 (1H, m), 2.68-2.56 (1H, m), 2.13-1.80 (3H, m), 1.61-1.51 (1H, m); ¹³C NMR (75.5 MHz, CD₃OD) δ 148.7, 129.2, 127.9, 125.8, 71.8, 57.4, 46.3, 37.2, 23.4; ESI TOF-MS m/z Calcd for C₁₁H₁₆NO [M+H]⁺ 178.12. found 178.14