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CAS No. : | 2629-72-3 | MDL No. : | MFCD00047457 |
Formula : | C8H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PZVZGDBCMQBRMA-UHFFFAOYSA-N |
M.W : | 137.18 | Pubchem ID : | 72923 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogenchloride; Adam?s catalyst; hydrogen; In methanol; water; under 60.006 Torr; for 46h;Inert atmosphere; | 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 32percent 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 15percent 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, 98percent) mp 58-60 °C. Rf = 0.2 (CH2Cl2/MeOH/28percent aq NH3 50:10:1). IR (Nujol) 3290, 1320 cm-1. 1H NMR (300 MHz, CD3OD) delta (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) delta (ppm) 31.5, 34.8, 35.2, 38.0, 47.9, 64.0. MS (ESI, MeOH) m/z (percent) 287 (36) [2M+H]+, 144 (100) [M+H]+. C8H17NO (143.2). |
palladium-carbon; In acetic acid; | a 3-(4-piperidinyl)propanol 3-(4-piperidinyl)propanol was prepared by hydrogenation of 3-(4-pyridyl)propanol in acetic acid in the presence of Pd/C according to the method described in J. Org. Chem., 1962, 27, 2966-2967. | |
With hydrogen;5% rhodium-on-charcoal; In water; at 50℃; under 15514.9 Torr; | Example 3 1-Methyl-4-Piperidinepropanol An Argonaut reaction vessel was charged with 4-pyridinepropanol (500.0 mg, 3.49 mmol) and 5percent Rh/C (62percent wet, 300.0 mg) in water (4.00 g). The resultant slurry was stirred at 500 RPM and the unit was pressurized with 300 psi of hydrogen. The resultant mixture was heated at 50° C. for about 4-4.5 h, during which time the hydrogen uptake ceased. The resultant mixture was then cooled to room temperature and a 37percent formaldehyde solution (340.0 mg, 4.19 mmol) was added in a single portion. The Argonaut vessel was sealed and the resultant slurry was stirred at 500 RPM, the unit was repressurized with 300 psi of hydrogen, and heated to 50° C. Hydrogen uptake ceased in about 1.2-1.5 h to yield the title compound, which was used in the next step without further purification or isolation. HPLC-MS analysis of an aliquot showed only C9H19NO MS: (Cl): m/z 158 (M++1) |
With platinum(IV) oxide; hydrogen; In acetic acid; at 40℃; under 38011.4 Torr; for 24h; | To a solution of 3- (pyridin-4-yl) propan-1-ol (20.0 g, 0.15 mol) in AcOH (300 mL) was added PtO2 (2.5 g, 11.0 mmol) . The mixture was sealed and stirred at 40 under 735 psi hydrogen for 24h. After cooling to rt, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The crude was dissolved with DCM (1L) and organic phase was washed with sat. Na2CO3 (100 mL × 3) , dried over anhydrous Na2SO4, filtered and concentrated to afford 3- (piperidin-4-yl) propan-1-ol which was used in next step without purification. LRMS m/z (M+H) 144.1 found, 144.1 required. |
[ 5223-06-3 ]
2-(5-Ethylpyridin-2-yl)ethanol
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