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CAS No. : | 135072-32-1 | MDL No. : | MFCD14584462 |
Formula : | C14H19NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JDVADOGJQJZIOJ-UHFFFAOYSA-N |
M.W : | 249.31 | Pubchem ID : | 15651196 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 72.12 |
TPSA : | 38.77 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) : | -6.61 cm/s |
Log Po/w (iLOGP) : | 2.66 |
Log Po/w (XLOGP3) : | 1.71 |
Log Po/w (WLOGP) : | 0.92 |
Log Po/w (MLOGP) : | 1.27 |
Log Po/w (SILICOS-IT) : | 2.1 |
Consensus Log Po/w : | 1.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.38 |
Solubility : | 1.04 mg/ml ; 0.00417 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.14 |
Solubility : | 1.81 mg/ml ; 0.00725 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.24 |
Solubility : | 0.142 mg/ml ; 0.00057 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.61 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
87% | Stage #1: at 20 - 65℃; for 66 h; Heating / reflux Stage #2: With potassium carbonate In water |
4-Benzyl-morpholihe-2-carboxylic acid ethyl ester (1); A stirred solution of 4-benzyl-morpholine-2-carbonitrile (113.0 g, 0.56 mol) in ethanol (1030 mL) is treated with concentrated sulphuric acid (165 mL) added in portions. (exothermic, internal temperature rises from ambient to 65 °C). The mixture is then warmed under reflux for 66hrs. The solution is cooled and then concentrated in vacuo to half volume, basified with aqueous potassium carbonate (beware frothing) and the product extracted into diethyl ether. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness in vacuo to yield an oil. This material is evacuated further under high vacuum. Yield = 121. 3g (87percent). |
87% | Stage #2: With sulfuric acid In water at 15 - 20℃; for 60.3333 h; Heating / reflux Stage #3: With sodium hydrogencarbonate; sodium carbonate In water; ethyl acetate at 20 - 25℃; for 0.25 h; |
Alternatively, compound 1 may be synthesised as follows: A 100 L reactor attached to a scrubber filled with IN NaOH (60 L) is charged under nitrogen atmosphere with 4-benzyl-morpholine-2-carbonitrile (1867 g, 9.23 mol) and ethanol (20 L). At Tmass = 15-20°C, concentrated sulfuric acid (2.76 L, 50 mol) is added to the solution over 20 min (highly exothermic). The solution is heated to reflux for 2.5 days. Then, 10 L of solvent is distilled off under vacuum and the reaction mixture is cooled to Tmass = 20-25°C. Water (40 L) is added over 25 min followed by Na2C03 solution (1/2 saturated, 18 L) and NaHC03 (1/2 saturated, 7 L) to reach a pH-7. Ethyl acetate is added (15 L) and the phases are mixed for 15 min. The organic phase is separated and the aqueous phase is extracted with ethyl acetate (2x10 L). The combined organic layers are evaporated to dryness under vacuum to give 1 as a yellow to brown oil (1992g, 87percent) |
87% | at 20 - 65℃; for 66 h; Heating / reflux | A stirred solution of 4-benzyl-morpholine-2-carbonitrile (113. 0g, 0.56mole) in ethanol (1030ml) is treated with concentrated sulphuric acid (165ml) added in portions. (exothermic, internal temperature rises from ambient to 65 °C). The mixture is then warmed under reflux for 66hrs. The solution is cooled and then concentrated in vacuo to half volume, basified with aqueous potassium carbonate (beware frothing) and the product extracted into diethyl ether. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness in vacuo to yield an oil. This material is evacuated further under high vacuum. Yield = 121.3g (87percent). |
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