2,2′-[(Phenylmethyl)imino]bis[ethanol]

K2CO3 (8.65 g, 62.58 mmol), and (bromomethyl)benzene (2.96g, 25 mmol) were added to a solution of 2, 2’-azanediyldiethanol (2.63 g, 53.08 mmol) in dry acetone (65 mL). The reaction mixture was heated to reflux overnight. The white suspension thus obtained was filtered and the solvent was evaporated to afford 5.6 g as a yellow liquid, which was dissolved in DCM and washed with water. The organic layer wasdried over sodium sulphate and concentrated under vacuum to afford the title compound (4.88, 100percent yield).HPLC-MS (Method A): Ret, 1.14 mm; ESl-MS m/z, 196 (M+l).To a stirred solution of diethanol amine (10.5 g, 100 mmol), and anhydrous K2CO3 (30 gm, excess) in dry acetone (250 ml), benzyl bromide (17.2 gm, 100 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extracted with chloroform and washed with H2O. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. Colorless oil. Yield: 19.0 g, 97percent; MS: 196 (M+H).To a stirred solution of diethanol amine (10.5 g, 100 mmol), and anhydrous K2CO3 (30 gm, excess) in dry acetone (250 ml), benzyl bromide (17.2 gm, 100 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extracted with chloroform and washed with H2O. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. Colorless oil. Yield: 19.0 g, 97percent; MS: 196 (M+H).2-[Benzyl-(2-hydroxyethyl)amino]ethanol (XIX); 16.9 ml (142 mmol) of benzyl bromide were added to a stirred solution of 15.0 g (142 mmol) of diethanolamine and 39.4 g (285 mmol) of potassium carbonate in 200 ml of acetone, and the solution was then heated under reflux for 3 h. The cooled reaction mixture was filtered and concentrated in vacuo. 100 ml of water were added, and the aqueous mixture was extracted with chloroform (3x60). The combined organic phases were washed with water and saturated NaCI solution and dried over magnesium sulfate, and the solvent was removed in vacuo. Yield: 26.9 g (96percent) of colorless oil The reaction product was converted into the hydrochloride by dissolving the residue in 70 ml of 5N ethereal HCI and removing the solvent in vacuo. The residue was then coevaporated with toluene twice. Yield: 31.7 g (99percent) of colorless oil To a stirred solution of diethanolamine 48 (21 g, 200 mmol) andanhydrous KReference Reference (a) (a) Potassium carbonate (60 g, 435 mmol) was suspended in acetone (500 ml). Diethanolamine (21 g, 200 mmol) and benzyl bromide (34.4 g, 200 mmol) were successively added. The reaction mixture was refluxed for 8 hours, cooled to room temperature and filtered. The filtrate was concentrated to dryness and then the residue was purified by silica gel column chromatography (dichloromethane/methanol: 10/1) to isolate product A in the form of a colourless oil (37.5 g, 75percent yield).A mixture of compound O-1 (12.10 g, 115.1 mmol), benzyl bromide (13.70 mL, 115.3 mmol) and potassium carbonate (31.81 g, 230.2 mmol) in acetone (120 mL) was refluxed for 18 hours, cooled to rt and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v) = 20/1) to give compound O-2 as pale yellow liquid (16.39 g, 72.9percent). The compound was characterized by the following spectroscopic data: A mixture of compound O-1 (12.10 g, 115.1 mmol), benzyl bromide (13.70 mL, 115.3 mmol) and potassiumcarbonate (31.81 g, 230.2 mmol) in acetone (120 mL) was refluxed for 18 hours, cooled to rt and filtered. The filtratewas concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v) = 20/1) togive compound O-2 as pale yellow liquid (16.39 g, 72.9percent). The compound was characterized by the following spectroscopicdata:1H NMR (400 MHz, CDCl3): δ 7.36-7.23 (m, 5H), 3.70 (s, 2H), 3.62 (t, J = 5.3 Hz, 4H), 2.72 (t, J = 5.3 Hz, 4H), 2.48(brs, 2H).Into a 500-mL round-bottom flask was placed 2, 2'-azanediyldiethanol (10 g, 95 mmol, 1 equiv), MeCN (140 mL), (bromomethyl)benzene (12 mL), and KA solution of 2, 2’-azanediylbis(ethan-l-ol) (198.15 g, 1.88 mol), K2C03 (520.95 g, 3.77 mol) and (bromomethyl)benzene (386.79 g, 2.26 mol) in acetonitrile (2000 mL) was stirred at90 °C for 2.5 h. After cooling to RT, the reaction mixture was filtered followed by EA (2 x lOOmL) wash. The filtrate was concentrated under reduced pressure. The residue was purified by silica chromatography (eluting with MeOH: DCM = 1: 10, v/v) to give 2, 2’-(benzylazanediyl)bis(ethan-l-ol) (89.44 g) as a colorless oil. MS: m/z 196 (M+H).(1) benzyl chloride (1.90g, 15mmol), diethanolamine (2.4g, 23mmol), anhydrous potassium carbonate (4.28g, 30mmol) and potassium iodide (0.5g) by adding 250 ml two bottles in, add 80 ml acetonitrile, nitrogen for 5 minutes, the air in the replacement system, then refluxing 12h. (2) stopping the reaction, steaming and removing the acetonitrile, adding dichloromethane 30 ml and water 30 ml, liquid. Water washing of the organic phase with two, in order to remove the excess of a di-ethanolamine. The product in water have a certain solubility, after washing, the aqueous phase and then dichloromethane is used for extraction of the two. Separating the organic phase, dried with anhydrous sodium sulfate. (3) steaming and remove the dichloromethane to be pale yellow liquid 2.69g, yield 91.8percent. TLC detection, ethyl acetate/petroleum ether=1:1 as the developing agent, the target product than the shift value RBenzyl amine (5.09 mL, 46.7 mmol) and 2-chloroethanol (9.38 mL, 140 mmol) were added together in a 250-mL flask. A solid sodium carbonate (7.42 g, 70 mmol) was added following with water (2 mL). The reaction was heating up in an oil bath to 112°C for 3 hrs. The reaction mixture was cool down and co- evaporated with MeOH (30 mL x 3). The residue was then dissolved in DCM and filtrated. The remaining residue was washed with DCM 3 times. The combined DCM was concentrated under reduced pressure and gave an oil-like product (4.78 g, 53percent yield) after high vacuo drying. LC-MS (ESI, MH

Molecular Weight:195.26
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:195.125928785
Monoisotopic Mass:195.125928785
Topological Polar Surface Area:43.7
Heavy Atom Count:14
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes