4-[2-(Dimethylamino)ethoxy]benzenemethanamine

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 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[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)[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)[00253] To a solution of 5-(6-methoxy-2-pyridyl)-2, 3-dihydro-1, 4-benzodioxine-3- carbaldehyde (50 mg, 1 eq, 0.18 mmol) in DCE (2 ml) under nitrogen atmosphere at RT were added In a 1000 ml reaction flask 400 ml of acetone will be added, 97 g (0.70 mol) of anhydrous potassium carbonate, P-Hydroxyphenylacetamide81 g (0.53 mol), Potassium iodide 2g, warmed to 45 C, maintained under stirring 45-60 C63.5 g (0.59 mol) of dimethylaminochloroethane was slowly added dropwise, and the dropwise addition was completed.Maintain 45-60 , heat for 10 hours, the end of cooling cooled to room temperature, Salt filtration, the filtrate was concentrated to dryness sodium pressure, Got it4- [2- (dimethylamino)Ethoxy] benzeneacetamide114.5 g (0.51 mol), Yield 96.2%The above intermediate was added 500ml of dichloromethane, Stirring all dissolved, and cooled to about 0 , Start dropping sodium hypochlorite solution (available chlorine content of 10%) 200g (0.56mol), dropping process, Always maintain the system temperature is less than 5 , dropping end, Keeping stirring for less than 5 C for 2 hours, then slowly warming to 55-60 C, And stirred at this temperature for 8 hours, stirring was completed, cooled to room temperature and then stratified, The organic phase was washed twice with water, dried over anhydrous magnesium sulfate, concentrated to dryness under reduced pressure to give a pale yellow oily liquid4- [2- (dimethylamino)Ethoxy] benzylamine95.2 g (0.49 mol), total yield 92.5%, HPLC purity 99.56%.(Mobile phase: 700 ml of water; methanol 200 ml. Detection wavelength:240 nm, flow rate 1.0 ml / min, sample 0.01 g, Diluted to 25 ml with mobile phase, injection volume 5mul)4- (2-dimethylaminoethoxy) benzyl bromide 129 g (0.5 mol)Urotropine 70g (0.5mo)Dissolved in 300 ml of methylene chloride, heated to reflux 8h, the reaction is over, recovery of dichloromethane, adding 250 ml of methanol, adding 250 g of concentrated hydrochloric acid, Flow reaction 1h, after the end of the reaction, cooled to room temperature, vacuum recovery of most of the solution, ice bath, with 1mol.L-1 sodium hydroxide Solution and the reaction solution, to pH to 9-10, 300 ml of ethyl acetate extraction, anhydrous sodium sulfate drying, recovery solvent, vacuum steam Distilled to give colorless liquid 90g, yield 93%,

Molecular Weight:194.27
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:194.141913202
Monoisotopic Mass:194.141913202
Topological Polar Surface Area:38.5
Heavy Atom Count:14
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes