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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.
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 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).]
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.
1-(4-((diethylamino)methyl)phenyl)ethan-1-one[ No CAS ]
Yield
Reaction Conditions
Operation 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.
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