N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide synthesis
- Product Name:N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide
- CAS Number:262368-30-9
- Molecular formula:C14H22N4O
- Molecular Weight:262.35
109-01-3
2653-16-9
262368-30-9
GENERAL STEPS: 2-Chloro-N-methyl-N-(4-nitrophenyl)acetamide (210.0 g, 0.9185 mol) was suspended in toluene (1157.56 mL) and heated to 40 °C. The mixture was then purified by aqueous solution of N-methylpiperazine (252.65 mL, 2.48 eq.). N-methylpiperazine (252.65 mL, 2.48 eq.) was added dropwise over 30 min. The reaction mixture was stirred at 55 °C for 2 hours. After cooling to room temperature, the reaction mixture was washed with water (157.23 mL) and the organic layer was diluted with isopropanol (1075.33 mL). Palladium/carbon catalyst (18.81 g) was added and hydrogenated overnight at 20 °C under 1 bar hydrogen pressure. After the reaction was complete, the catalyst was removed by filtration and the filtrate was concentrated to about 150 mL and ground with ether (120.0 mL). The crystalline product was collected by filtration, washed with ether and dried under vacuum to afford N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 170 g (70.5% yield).
109-01-3
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79-04-9
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100-15-2
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262368-30-9
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Yield:262368-30-9 79.27%
Reaction Conditions:
Stage #1:chloroacetyl chloride;N-methyl(p-nitroaniline) in ethyl acetate at 50 - 55; for 2 h;
Stage #2:1-methyl-piperazine at 45 - 50; for 4.5 h;Solvent;
Steps:
3 Example 3: Preparation of Compound TM
40 g of N-methyl-4-aminonitrobenzene and 320 ml of ethyl acetate were added to a 1-liter three-necked flask at 20 to 25 ° C over 30 minutesA mixed solution of 31.2 g (1.05 eq) of chloroacetyl chloride and 80 ml of ethyl acetate was added dropwise to the reaction solution. Dripping finished, heated to 50 ~ 55 , PaulTemperature reaction for 2 hours, TLC monitoring reaction point disappeared (the development of ethyl acetate: petroleum ether = 2: 1, Rf = 0.42), cooled to 20 ~ 25 ,40 ml of water was added to the reaction solution, stirred for 15 minutes, and the organic phase was poured into a 1-liter three-necked flask. Control the temperature at 20 ~ 25 , will be 65.80G (2.5 eq)N-methylpiperazine was added dropwise to the reaction flask,Drop finished,Heated to 45 ~ 50 ,Insulation reaction for 4.5 hours, TLC monitoring reactionThe disappearance of the dross (developing solvent: dichloromethane: methanol = 2: 1, Rf = 0.61)Cooling to 10 ~ 15 , adding 120 ml of 28% ammonia and 120 ml of water,Add 140 grams (3.0eq) of insurance powder in batches,Plus heating, heating to 50 ~ 55 , insulation reaction 2.5 hours, TLC monitoring reaction pointDisappeared (developing agent for dichloromethane: methanol = 2: 1,Rf = 0.46), cooled to 20-25 ° C, separated, 50 ml of ethyl acetate, washed with water, 50Ml saturated brine, dried over anhydrous sodium sulfate, concentrated, the residue by adding 80 ml of ethyl acetate to recrystallize, filter, filter cake 45 blastDried to give 54.67 g of a white powder in a yield of 79.27%. Purity: 98.91%.
References:
Langfang Bairui Chemical Co., Ltd;Jiao, Shaolai;Wang, Jian CN106467500, 2017, A Location in patent:Paragraph 0034; 0036; 0037; 0038
109-01-3
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2653-16-9
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262368-30-9
279 suppliers
$5.00/250mg
1139453-98-7
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262368-30-9
279 suppliers
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100-15-2
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$10.00/1g
262368-30-9
279 suppliers
$5.00/250mg
2653-16-9
144 suppliers
inquiry
262368-30-9
279 suppliers
$5.00/250mg