piperidine-4-propanol synthesis
- Product Name:piperidine-4-propanol
- CAS Number:7037-49-2
- Molecular formula:C8H17NO
- Molecular Weight:143.23
2629-72-3
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7037-49-2
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Yield:7037-49-2 98%
Reaction Conditions:
with hydrogenchloride;Adam’s catalyst;hydrogen in methanol;water under 60.006 Torr; for 46 h;Inert atmosphere;
Steps:
8 4.1.8
4-(3-Hydroxypropyl)piperidine (17)
Under an atmosphere of argon platinum(IV)oxide (1.45 g, 6.4 mmol) was added to a solution of 16 (10.0 g, 72.89 mmol) in MeOH (110 mL) and 32% hydrochloric acid (18 mL).
The mixture was vigorously stirred under a low pressure of hydrogen (8 kPa) for 46 h.
The major part of the catalyst was removed by filtration and the volatiles were removed under reduced pressure.
The oily residue was taken up in 15% aq NaOH (80 mL) and the product was extracted with CH2Cl2 (150 and 3 * 100 mL).
The pooled extracts were washed with water (20 mL) and dried over Na2SO4.
Evaporation of the volatiles and drying in vacuo yielded product 17 as a white crystalline, compact solid (10.3 g, 98%) mp 58-60 °C. Rf = 0.2 (CH2Cl2/MeOH/28% aq NH3 50:10:1). IR (Nujol) 3290, 1320 cm-1. 1H NMR (300 MHz, CD3OD) δ (ppm) 1.08-1.23 (m, 2H), 1.27-1.36 (m, 2H), 1.36-1.49 (m, 1H), 1.53-1.63 (m, 2H), 1.74 (br d, 2H, J ca 13.4 Hz), 2.59 (dt, 2H, J 12.4 2.6 Hz), 3.04 (td, 2H, J 12.4 2.9 Hz), 3.56 (t, 2H, J 6.6 Hz).
13C NMR (75 MHz, CD3OD) δ (ppm) 31.5, 34.8, 35.2, 38.0, 47.9, 64.0. MS (ESI, MeOH) m/z (%) 287 (36) [2M+H]+, 144 (100) [M+H]+. C8H17NO (143.2).
References:
Keller, Max;Tränkle, Christian;She, Xueke;Pegoli, Andrea;Bernhardt, Günther;Buschauer, Armin;Read, Roger W. [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 14,p. 3970 - 3990]
93524-95-9
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7037-49-2
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156185-63-6
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$24.00/250mg
7037-49-2
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71879-55-5
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$190.00/500mg
7037-49-2
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15854-87-2
320 suppliers
$6.00/1g
7037-49-2
141 suppliers
$19.00/250mg