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CAS No. : | 10315-06-7 | MDL No. : | MFCD09750949 |
Formula : | C14H19NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MXOZSPRDEKPWCW-UHFFFAOYSA-N |
M.W : | 233.31 | Pubchem ID : | 11436222 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 71.04 |
TPSA : | 29.54 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 2.87 |
Log Po/w (XLOGP3) : | 2.1 |
Log Po/w (WLOGP) : | 1.54 |
Log Po/w (MLOGP) : | 2.12 |
Log Po/w (SILICOS-IT) : | 2.36 |
Consensus Log Po/w : | 2.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.61 |
Solubility : | 0.577 mg/ml ; 0.00247 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.35 |
Solubility : | 1.04 mg/ml ; 0.00446 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.38 |
Solubility : | 0.0975 mg/ml ; 0.000418 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.92 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
88% | With triethylamine In chloroform at 20℃; | To A solution of METHYL PIPERIDINE-4-CARBOXYLATE (10. 00 G, 6. 4 MMOL) AND triethylamine (10. 32 G, 10. 2 MMOL) IN CHC13 (100 ML), BENZYL BROMIDE (14. 69 G, 8. 6 mmol) was added under argon atmosphere while cooling with a water and ice bath. The mixture was stirred at room temperature overnight. CHCI3 and water were added and the two phases were separated. The aqueous phase was extracted with CHCI3. The organic phase was dried over NA2S04 and concentrated to dryness, to afford 13. 80 G OF THE DESIRED COMPOUND AS AN ORANGE solid (YIELD : 88percent) |
78% | With potassium carbonate In acetonitrile at 85℃; Inert atmosphere | General procedure: A mix of methyl piperidine-4-carboxylate or ethyl 2-(piperidin-4-yl)acetate (10 mmol) in acetonitrile (20 ml), 1a–j (11 mmol),anhydrous K2CO3 (12 mmol) was refluxed under nitrogen for 8 hat 85 C. The mixture was then cooled and filtered and the solvent removed in vacuum. The residue was dissolved in ethyl acetate(50 ml) and washed with water (15 ml). Drying and removal of the solvent followed by chromatography (ethyl acetate/petroleumether = 1:4) afforded desired product 2a–j. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.6% | With triethylamine In 1,2-dichloro-ethane at 10 - 20℃; for 1.5 h; Reflux; Large scale | In the 1000L reactor, 360 kg of 1,2-dichloroethane was recovered in Example 2, and 69.54 kg of new 1,2-dichloroethane was added.Under stirring, 143.18 kg of methyl piperidinecarboxylate and 121.43 kg of triethylamine were added, and benzyl chloride 139.24 kg was added dropwise at a temperature of 10 to 20°C.After the dripping is completed, the temperature is gradually raised to reflux for 1.5 hours. The reaction of the raw material is completely cooled to 20 to 30° C., and 150 kg of water is added for 30 minutes to separate the liquid.The organic layer was dried, filtered, and the filtrate was concentrated to obtain 230.04 kg of methyl N-benzyl-4-piperidinecarboxylate;The molar yield was 98.6percent and the purity was 99.61percent.The 1,2-dichloroethane was recovered for the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | With sodium hydrogencarbonate In ethanol for 3 h; Reflux; Large scale | The 1.62kg4- piperidine carboxylic acid methyl ester hydrochloride, 1.08kg, put benzyl chloride, 1.89kg and 4.3kg of sodium bicarbonate was added to the ethanol 20L reactor, heated to reflux and maintained at reflux the reaction 3h, cooled to an inner temperature of 30 about deg.] C, discharge, filtered, and the filter cake washed with ethanol 2.15kg, drained, the filtrate was concentrated paste, the residue is dispersed in 4.7kg of toluene and 6.0kg of pure water, the organic layer was washed with stirring, separate the organic layer, the toluene was concentrated to give 1-benzyl-4-piperidine carboxylic acid methyl ester 1.92kg, as a pale yellow oily liquid. Yield: 96.5percent (in terms benzyl chloride). HPLC: 99.12percent |
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