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[ CAS No. 69293-74-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 69293-74-9
Chemical Structure| 69293-74-9
Chemical Structure| 69293-74-9
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Product Details of [ 69293-74-9 ]

CAS No. :69293-74-9 MDL No. :MFCD09948026
Formula : C12H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :XWLYXADFVFHUKA-UHFFFAOYSA-N
M.W : 188.27 Pubchem ID :24708414
Synonyms :

Calculated chemistry of [ 69293-74-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.25
TPSA : 27.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.72
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 2.25
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 2.46
Consensus Log Po/w : 2.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.45
Solubility : 0.664 mg/ml ; 0.00353 mol/l
Class : Soluble
Log S (Ali) : -2.41
Solubility : 0.729 mg/ml ; 0.00387 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.81
Solubility : 0.0292 mg/ml ; 0.000155 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 69293-74-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 69293-74-9 ]

* 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.

  • Downstream synthetic route of [ 69293-74-9 ]

[ 69293-74-9 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 69293-74-9 ]
  • [ 84227-70-3 ]
YieldReaction ConditionsOperation in experiment
67% With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 12h; Inert atmosphere; o-(Diethylaminomethyl)benzylamine (6) General procedure: o-(Diethylaminomethyl)benzonitrile (13) (6.0 g, 32 mmol) in anhydrous diethylether (20 mL) was added dropwiseover a period of 10 min to a suspension of LiAlH4 (2.4 g, 64 mmol) in anhydrous diethylether (50 mL, 0°C, N2 atmosphere). The mixture was allowed to come to room temperature,stirred for 12 h, cooled in ice, treated dropwise with 20% NaOH (17 mL) with cooling, andextracted three times with ether (50 mL each). The combined organic phases were dried overNa2SO4, filtered, and evaporated under vacuum. The product was collected as reddish-orangecolored oil.
With tetralin; nickel at 70℃; Hydrogenation;
  • 2
  • [ 69293-74-9 ]
  • [ 62642-59-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
  • 3
  • [ 109-89-7 ]
  • [ 17201-43-3 ]
  • [ 69293-74-9 ]
YieldReaction ConditionsOperation in experiment
86% In tetrahydrofuran at 20℃; for 1.5h; o-(Diethylaminomethyl)benzonitrile (13) General procedure: Dropwise additionof o-cyanobenzylbromide (12) (10.0 g, 50 mmol) in ethanol (30mL) to cold diethylamine (57mL, 0.55 mol) was followed by 3 h of stirring at room temperature. The solution becameorange and a white precipitate was observed. Aqueous Na2CO3 (20 mL, 0.1 M) was added untilthe solution became basic to pH paper. At this time the white precipitate dissolved. Then thesolution was concentrated and extracted into an ether layer. The organic layer was washed withwater 3 times, dried over Na2SO4, and evaporated under vacuum to yield the product as a reddish-orange oil.
With ethanol
With diethyl ether
  • 4
  • [ 70135-28-3 ]
  • [ 109-89-7 ]
  • [ 4381-02-6 ]
  • [ 6292-62-2 ]
  • [ 69293-74-9 ]
  • [ 104-85-8 ]
  • 4-(2-Ethylamino-propyl)-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Irradiation;
  • 5
  • [ 70135-28-3 ]
  • [ 109-89-7 ]
  • [ 4381-02-6 ]
  • [ 69293-74-9 ]
  • [ 104-85-8 ]
  • 4-(2-Ethylamino-propyl)-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Irradiation; Yield given;
  • 6
  • [ 105-07-7 ]
  • [ 13686-66-3 ]
  • [ 69293-74-9 ]
YieldReaction ConditionsOperation in experiment
84% With titanium tetrachloride In dichloromethane at 20℃; for 36h;
  • 7
  • [ 69293-74-9 ]
  • 4-diethylaminomethyl-benzoic acid-(2-diethylamino-ethyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: pyridine; thionyl chloride
  • 8
  • [ 69293-74-9 ]
  • 4-diethylaminomethyl-benzoic acid-(3-diethylamino-propyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: benzene; thionyl chloride
  • 9
  • [ 69293-74-9 ]
  • [ 78329-96-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: benzene; thionyl chloride
  • 10
  • [ 69293-74-9 ]
  • [ 91271-57-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Raney nickel; tetralin / 70 °C / 58840.6 Torr / Hydrogenation 2: sodium nitrite; aqueous acetic acid / zuletzt unter Erwaermen
  • 11
  • [ 69293-74-9 ]
  • diethyl-(4-chloromethyl-benzyl)-amine; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Raney nickel; tetralin / 70 °C / 58840.6 Torr / Hydrogenation 2: sodium nitrite; aqueous acetic acid / zuletzt unter Erwaermen 3: ethanol; hydrogen chloride
  • 12
  • [ 69293-74-9 ]
  • benzoic acid-(4-diethylaminomethyl-benzyl ester); hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Raney nickel; tetralin / 70 °C / 58840.6 Torr / Hydrogenation 2: sodium nitrite; aqueous acetic acid / zuletzt unter Erwaermen 3: benzene
  • 13
  • [ 109-01-3 ]
  • [ 69293-74-9 ]
  • [ 125743-63-7 ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 18h; W.a Intermediates Example W; 4- [[ (4-METHYLPIPERAZIN-1-YL) METHYL] BENZALDEHYDE]; a. 4- [[ (4-METHYLPIPERAZIN-1-YL) METHYL] BENZONITRILE] [4-[(DIETHYLAMINO) METHYL] BENZONITRILE] (250 mg, 1.28 [MMOL)] in DMF (25 mL) was treated with [1-METHYLPIPERAZINE] (191 mg, 1.91 mmol) followed by potassium carbonate (177 mg, 1.28 [MMOL).] The mixture was stirred at RT for ca. 18 h. The reaction was concentrated and then partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over [NA2SO4,] and concentrated to give pure product as a white solid (189mg, yield 69%). 'H NMR (300 MHz, DMSO) 8 7.78 (d, 2H), 7.49 (d, 2H), 3.53 (s, 2H), 2.44-2. 21 (m, 8H), 2.14 (s, [3H).]
  • 14
  • [ 109-89-7 ]
  • [ 874-86-2 ]
  • [ 69293-74-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; 43.43.1 43.1 1-{4-[(Diethylamino)methyl]phenyl}ethanone; 5.3 g of diethylamine were added to 10 g of 4-[chloromethyl]benzonitrile (65.96 mmol), 18.24 g of K2CO3 and 1.1 g of Kl in 150 ml of N,N-dimethylformamide at room temperature, and the mixture was stirred at room temperature until the reaction was complete. The mixture was then poured into ice-water and extracted with diethyl ether, and the organic phase was washed with saturated NaCI solution, dried and evaporated, resulting in 12.1 g of 4-[diethylaminomethyl]benzonitrile as an oil. ESI-MS [M+H]+= 189.05.
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; 43.1 Example 43; N-(3-Amino-1-benzyl-2,3-dioxopropyl)-2-(3-{4-[(diethylamino)methyl]phenyl}-1H-pyrazol-1-yl)nicotinamide hydrochloride; 43.1 1-{4-[(Diethylamino)methyl]phenyl}ethanone; 5.3 g of diethylamine were added to 10 g of 4-[chloromethyl]benzonitrile (65.96 mmol), 18.24 g of K2CO3 and 1.1 g of KI in 150 ml of N,N-dimethylformamide at room temperature, and the mixture was stirred at room temperature until the reaction was complete. The mixture was then poured into ice-water and extracted with diethyl ether, and the organic phase was washed with saturated NaCl solution, dried and evaporated, resulting in 12.1 g of 4-[diethylaminomethyl]benzonitrile as an oil.ESI-MS [M+H]+=189.05.
  • 15
  • [ 69293-74-9 ]
  • [ 75-16-1 ]
  • 1-(4-((diethylamino)methyl)phenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: p-(diethylaminomethyl)benzonitrile; methylmagnesium bromide In diethyl ether; toluene at 20℃; Heating / reflux; Stage #2: With sodium hydroxide; water 43.43.1 A solution of 12.1 g of 4-[diethylaminomethyl]benzonitrile in 40 ml of toluene was added to a solution of methylmagnesium bromide (43 ml of a 3 M solution in diethyl ether) in 40 ml of toluene, and the mixture was heated to reflux. Completion of the reaction was followed by pouring into ice-water, extracting with methyl tert-butyl ether, adjusting the aqueous phase to pH 11-12 by adding NaOH, and renewed extracting with methyl tert- butyl ether. The organic phase was dried and the solvent was evaporated. 12.1 g of the title compound were obtained. ESI-MS [M+H]+= 206.15.
Stage #1: p-(diethylaminomethyl)benzonitrile; methylmagnesium bromide In diethyl ether; toluene Heating / reflux; Stage #2: With sodium hydroxide; water In diethyl ether; tert-butyl methyl ether; toluene at 0℃; 43.1 A solution of 12.1 g of 4-[diethylaminomethyl]benzonitrile in 40 ml of toluene was added to a solution of methylmagnesium bromide (43 ml of a 3 M solution in diethyl ether) in 40 ml of toluene, and the mixture was heated to reflux. Completion of the reaction was followed by pouring into ice-water, extracting with methyl tert-butyl ether, adjusting the aqueous phase to pH 11-12 by adding NaOH, and renewed extracting with methyl tert-butyl ether. The organic phase was dried and the solvent was evaporated. 12.1 g of the title compound were obtained.ESI-MS [M+H]+=206.15.
  • 16
  • [ 69293-74-9 ]
  • 7-chloro-N-(4-((diethylamino)methyl)benzyl)quinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 12 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate; triethylamine / 1-methyl-pyrrolidin-2-one / 15 h / Inert atmosphere; Reflux
  • 17
  • [ 109-89-7 ]
  • [ 105-07-7 ]
  • [ 69293-74-9 ]
YieldReaction ConditionsOperation in experiment
46% With 1-hydrosilatrane In acetonitrile at 70℃; for 42h; Sealed tube; Green chemistry;
  • 18
  • [ 616-39-7 ]
  • [ 623-00-7 ]
  • ethyl[1-(4-cyanophenyl)ethyl](methyl)amine [ No CAS ]
  • [ 69293-74-9 ]
YieldReaction ConditionsOperation in experiment
With di-tert-butyl peroxide at 120℃; for 24h; Overall yield = 55 %; regioselective reaction;
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