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[ CAS No. 20059-73-8 ] {[proInfo.proName]}

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Chemical Structure| 20059-73-8
Chemical Structure| 20059-73-8
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Product Details of [ 20059-73-8 ]

CAS No. :20059-73-8 MDL No. :MFCD01075231
Formula : C11H18N2O Boiling Point : -
Linear Structure Formula :- InChI Key :OBHPRQNPNGQGCK-UHFFFAOYSA-N
M.W : 194.27 Pubchem ID :88349
Synonyms :

Calculated chemistry of [ 20059-73-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.92
TPSA : 38.49 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) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 0.66
Log Po/w (WLOGP) : 0.93
Log Po/w (MLOGP) : 1.24
Log Po/w (SILICOS-IT) : 1.27
Consensus Log Po/w : 1.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.45
Solubility : 6.93 mg/ml ; 0.0357 mol/l
Class : Very soluble
Log S (Ali) : -1.04
Solubility : 17.5 mg/ml ; 0.0903 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.11
Solubility : 0.152 mg/ml ; 0.000782 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 20059-73-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20059-73-8 ]

* 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 [ 20059-73-8 ]
  • Downstream synthetic route of [ 20059-73-8 ]

[ 20059-73-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 15182-92-0 ]
  • [ 20059-73-8 ]
YieldReaction ConditionsOperation in experiment
84.7%
Stage #1: With hydroxylamine hydrochloride In water; acetic acid at 0 - 5℃; for 2 h;
Stage #2: With acetic acid; zinc In water at 45 - 70℃; for 7 h;
27 kg of 80percent acetic acid are charged into a reactor, 5.3 kg of hydroxylamine hydrochloride are added, the mixture is cooled to 0-5 °C and the solution prepared in the previous step containing 13.5 kg of 100percent 4-(2-dimethylaminoethoxy)- benzaldehyde in acetic solution is added. The reaction mixture is kept at 0-5°C for at least 2 hours. EPO <DP n="7"/>When the reaction is complete, 10.8 kg of powdered zinc are added in portions, allowing the temperature to rise up to a maximum of 50 °C.This mixture is kept under stirring at 45-50°C for at least 5 hours, and then heated to 65-70°C for at least 2 hours. Upon completion of the reaction, the reaction mixture is distilled to obtain a dense but stirrable residue.20.3 kg of deionized water are then added to the residue thus treated, the mixture thus obtained is cooled to 20-30°C and 54 kg of 30percent ammonia are added dropwise. The reaction mixture is then stirred at 20-30°C for at least 10 minutes, the pH is checked to ensure it is above 9.5. The reaction mixture is then extracted at 20-25 °C with 40.5 kg of methylene chloride. The organic phase is separated while the aqueous phase is reextracted with 27 kg of methylene chloride and the mixture is stirred for at least 5 minutes; the organic phase is added to the previous organic phase. Then the solvent is removed until an oily residue is obtained. 54 kg of sec-butanol and 20.3 kg of N, N - dimethylformamide are added. The solution thus obtained contains 11.5 kg of 4-(2-dimethylaminoethoxy)-benzylamine Yield: 84.7percent.
Reference: [1] Patent: WO2006/51079, 2006, A1, . Location in patent: Page/Page column 5-6
[2] Patent: US2879293, 1957, ,
[3] Organic Process Research and Development, 2013, vol. 17, # 7, p. 981 - 984
[4] Patent: KR101819771, 2018, B1, . Location in patent: Paragraph 0023; 0045-0052
  • 2
  • [ 131028-55-2 ]
  • [ 20059-73-8 ]
YieldReaction ConditionsOperation in experiment
95.2% With ammonium hydroxide In methanol at 80℃; for 6 h; Autoclave 50g (0.2mol) Compound XII is added 300ml of methanol, 170g of 20percent aqueous ammonia, sealed in an autoclave and heated to 80 deg. C for 6 hours, cooled, and concentrated to give 38.1g oil IX, a yield of 95.2percent
Reference: [1] Patent: CN105985257, 2016, A, . Location in patent: Paragraph 0007; 0015
  • 3
  • [ 24197-95-3 ]
  • [ 20059-73-8 ]
YieldReaction ConditionsOperation in experiment
80% With sodium tetrahydroborate In ethanol; water for 20 h; Heating / reflux [Example 3]; Preparation of 4-[2-(dimethylamino)ethoxy Ibenzylamine: reduction reaction by theformula 3; 2g(10.5mmol) of 4-[2-(dimethylamino)ethoxy]benzonitrile was dissolved in 30mNo.of ethanol, and 0.23(0.92mmol) of copper(II)sulfate-5 hydrate(2mol aqueous solution)was added thereto. And 1.74g(45.94mmol) of sodium borohydride was slowlydropwised, followed by refluxing and mixing for 20 hours. The reactant was cooled down to room temperature, and extracted withethylacetate, and dried with magnesium sulfate anhydrous, and then 1.63g(80percent yield)of a desired product was obtained by decompression and concentration.'HNMRCCDQ ,ppm): 1.63(br,NH ), 2.30(s,6H), 2.66-2.7l(t,2H), 3.77(s,2H),3 24.01~4.06(t,2H), 6.83~6.88(d,2H), 7.15~7.20(d,2H)
Reference: [1] Patent: WO2004/13082, 2004, A2, . Location in patent: Page/Page column 10
[2] Patent: WO2006/11696, 2006, A1, . Location in patent: Page/Page column 8-9
[3] Patent: WO2004/13082, 2004, A2, . Location in patent: Page/Page column 9,10
[4] Patent: WO2004/13082, 2004, A2, . Location in patent: Page/Page column 9
  • 4
  • [ 140-75-0 ]
  • [ 20059-73-8 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: at 130 - 140℃; for 1 h;
Stage #2: at 130 - 140℃; for 5 h;
[Example 1]; Preparation of 4- [2- (dimethyl amino)ethoxy Ibenzylamine; 2.54g(63.43mmol) of 60percent sodium hydride was slowly dropwised to6.63g(74.37mmol) of 2-(dimethylamino)ethanol at 0°C.After finishing the drop wise, the temperature of reactor was raised to 130~140°Cand mixed for 1 hour. 5.48g(43.79mmol) of 4-fluorobenzylamine was slowlydropwised therein, followed by mixing at 130~140°C for 5 hours. After finishing thereaction, the reactant was cooled down to room temperature. 100mNo. of H O was addedthereto, followed by mixing for 30 minutes, and then extracted withchloroform(150mNo.x2), and dried with magnesium sulfate anhydrous, which was thenfiltered, and 7.74g(91percent yield) of a desired product was obtained by decompressing -distilling.,ppm): 1.63(br,NH ), 2.31(s,6H), 2.67~2.72(t,2H), 3.77(s,2H),4.00~4.05(t,2H), 6.84~6.89(d,2H), 7.17~7.21(d,2H)
Reference: [1] Patent: WO2006/11696, 2006, A1, . Location in patent: Page/Page column 7-8
  • 5
  • [ 123-08-0 ]
  • [ 20059-73-8 ]
Reference: [1] Patent: US2879293, 1957, ,
[2] Organic Process Research and Development, 2013, vol. 17, # 7, p. 981 - 984
[3] Patent: KR101819771, 2018, B1,
  • 6
  • [ 149505-94-2 ]
  • [ 20059-73-8 ]
Reference: [1] Antimicrobial Agents and Chemotherapy, 2016, vol. 60, # 8, p. 4442 - 4452
  • 7
  • [ 696-60-6 ]
  • [ 20059-73-8 ]
Reference: [1] Antimicrobial Agents and Chemotherapy, 2016, vol. 60, # 8, p. 4442 - 4452
  • 8
  • [ 108-95-2 ]
  • [ 20059-73-8 ]
Reference: [1] Patent: CN105985257, 2016, A,
  • 9
  • [ 13468-02-5 ]
  • [ 20059-73-8 ]
Reference: [1] Patent: CN105985257, 2016, A,
  • 10
  • [ 106-44-5 ]
  • [ 20059-73-8 ]
Reference: [1] Patent: CN106748821, 2017, A,
  • 11
  • [ 20059-73-8 ]
  • [ 554-92-7 ]
Reference: [1] Organic Process Research and Development, 2013, vol. 17, # 7, p. 981 - 984
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