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[ CAS No. 135072-32-1 ] {[proInfo.proName]}

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Chemical Structure| 135072-32-1
Chemical Structure| 135072-32-1
Structure of 135072-32-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 135072-32-1 ]

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 :

Calculated chemistry of [ 135072-32-1 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 135072-32-1 ]

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:

Application In Synthesis of [ 135072-32-1 ]

* 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.

  • Upstream synthesis route of [ 135072-32-1 ]
  • Downstream synthetic route of [ 135072-32-1 ]

[ 135072-32-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 135072-32-1 ]
  • [ 135782-25-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 6, p. 683 - 689
[2] Tetrahedron Letters, 1991, vol. 32, # 20, p. 2281 - 2284
  • 2
  • [ 64-17-5 ]
  • [ 147767-51-9 ]
  • [ 135072-32-1 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Patent: WO2005/47272, 2005, A1, . Location in patent: Page/Page column 49-50
[2] Patent: WO2005/47272, 2005, A1, . Location in patent: Page/Page column 50
[3] Patent: WO2005/60949, 2005, A2, . Location in patent: Page/Page column 276
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 6, p. 683 - 689
[5] Tetrahedron Letters, 1991, vol. 32, # 20, p. 2281 - 2284
  • 3
  • [ 104-63-2 ]
  • [ 135072-32-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 6, p. 683 - 689
[2] Tetrahedron Letters, 1991, vol. 32, # 20, p. 2281 - 2284
  • 4
  • [ 1030837-46-7 ]
  • [ 135072-32-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 6, p. 683 - 689
  • 5
  • [ 24424-99-5 ]
  • [ 135072-32-1 ]
  • [ 768371-16-0 ]
Reference: [1] Patent: WO2004/74291, 2004, A1, . Location in patent: Page 66-67
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