Synthesis and application of aromatic amine acetylcholin esterase inhibitor containing amino side chains
A kind of side chain, aromatic technology, applied in the field of aromatic amine acetylcholinesterase inhibitors, can solve the problem that the inhibitory activity of acetylcholinesterase or phosphodiesterase 5 is not disclosed and the like
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example 1
[0046] Example 1 N-(4-chlorophenyl)-4-(1-morpholinomethyl)benzamide (I 1 ) preparation
[0047] Preparation of 4-bromomethylbenzoic acid: 3.00g of p-toluic acid, 4.00g of NBS and 0.1g of AIBN, in a 100ml round bottom flask, add 40ml of carbon tetrachloride, reflux reaction at 90°C, spot plate tracking to The raw material reacted completely, about 1.5h, after cooling, it was suction filtered, the filter cake was washed with warm water to remove the succinimide produced in the reaction, and then dried to obtain 4.02g of white solid product with a yield of 84%.
[0048] Preparation of 4-bromomethylbenzoyl chloride: Add 4g of p-bromomethylbenzoic acid to a 100ml round-bottomed flask equipped with a tail gas absorption and reflux tube, then add about 10ml of thionyl chloride, heat to 60°C for reaction 2 -4 hours, until the solid is completely dissolved, no gas is released from the tail gas absorption device, the solvent thionyl chloride is evaporated as much as possible under redu...
example 2
[0081] Example 2 4-(4-piperidinylmethyl-benzamido)methyl benzoate
[0082] The preparation of methyl p-aminobenzoate: in the 100ml three-necked flask that tail gas absorbing device is housed, thermometer and reflux condenser, add 2.76g (0.02mol) p-hydroxybenzoic acid, then add 30ml methyl alcohol and make it dissolve, in ice-water bath Slowly add about 5ml of thionyl chloride dropwise, during which a large amount of white solids appear. After the dropwise addition is completed, the temperature is raised to reflux conditions. After reacting for 2 hours, part of the methanol is recovered by rotary evaporation, and then cold water is added to completely dissolve the solids. Adjust the pH with ammonia water To weak alkalinity, a large amount of white solid precipitated, filtered, the filter cake was washed with cold water, and dried under vacuum to obtain 2.53 g of white solid, yield: 84%.
[0083] Preparation of 4-(4-(bromomethyl)benzamido)methyl benzoate: The method is the same ...
example 3
[0087] Example 3 4-(4-morpholino)aniline
[0088] Preparation of 4-(4-nitrophenyl)morpholine: Weigh 3.16g (0.02mol) p-nitrochlorobenzene in a 100ml round bottom flask, add 25ml dimethyl sulfoxide to dissolve, add 2.62g (0.03mol ) morpholine, the solution turned yellow immediately after adding, controlled the temperature in an oil bath to react at 100°C, followed the reaction by TLC, and the reaction was completed in about 10 hours. The solid precipitated, and the solid was filtered with suction, and the filter cake was washed with cold water. The filter cake was recrystallized with a large amount of water, and dried to obtain 3.82 g of a yellow solid, with a yield of 92%.
[0089] Preparation of 4-(4-morpholino)aniline: Weigh 4g iron powder in a 100ml round bottom flask, add 30ml water and 0.5ml glacial acetic acid, activate under reflux for 10min, then weigh 3.12g (0.015mol) Add the 4-(4-nitrophenyl)morpholine synthesized in one step into the reaction flask in 20ml of methan...
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