2-[Bis(phenylmethyl)amino]ethanol

Dibenzylaminoethanol:; To a 250 mL round bottom flask equipped with stirbar, reflux condensor, nitrogen inlet, and septum was added potassium carbonate (56.5 g, 0.41 mol), ethanol (80 mL), and ethanolamine (9.9 mL, 0.16 mol). The stirred solution was heated to reflux and benzyl chloride (37.9 mL, 0.33 mol) was added via syringe. The resulting solution was stirred for 16 hours at reflux, allowed to cool, then poured into water (200 mL). The solution was extracted with chloroform (3x300 mL). The combined organic layers were dried with magnesium sulfate, filtered, then evaporated to dryness. Recrystallization from hexanes yielded the product as colorless crystals (32.8 g, 83 percent). Dibenzylamino Ethanol Benzyl chloride (278.5g, 2.2 mol), ethanol amine (60 mL, 1 mol), potassium carbonate (283.1g, 2.05mol) and ethanol (2 L) were mixed together in a 3L 3- neck flask, fitted with an overhead stirrer, a condenser and a glass plug. The apparatus was heated up to reflux for 36 hr, after which the insoluble solid was filtered through a medium frit. The filtrate was recovered and ethanol was removed by rotoary evaporation. The viscous liquid was redissolved in ether, the solid suspension removed by filtration and extracted twice against water. The ether solution was kept and the aqueous layer was extracted twice with dichloromethane (2 x 400 mL). The fraction were recombined, dried over MgSOBenzyl chloride (278.5 g, 2.2 mol), ethanol amine (60 mE, 1 mol), potassium carbonate (283.1 g, 2.05 mol) and ethanol (2 E) were mixed together in a 3 E 3-neck flask, fitted with an overhead stirrer, a condenser and a glass plug. The apparatus was heated up to reflux for 36 hr, after which the insoluble solid was filtered through a medium frit. The filtrate was recovered and ethanol was removed by rotary evaporation. The viscous liquid was redissolved in ether, the solid suspension removed by filtration and extracted twice against water. The ether solution was kept and the aqueous layer was extracted twice with dichioromethane (2x400 mE). The fraction were recombined, dried over MgSO4, stirred over carbon black for 15 mm and filtered through a celite pad. Dichloromethane was removed and the solid was redissolved into a minimal amount of ether (combined volume of 300 mE with the first ether fraction, 300 mE). Rexanes (1700 mE) was added and the solution was heated up gently till complete dissolution ofthe product. The solution was then cooled down gently, placed in the fridge (+4° C.) overnight and white crystals were obtained. The recrystallization was done a secondtime. 166.63 g, 69percent yield. ‘RNMR(d5-DMSO)ö 7.39- 7.24 (bR), 4.42 (1R), 3.60 (4R), 3.52 (2R), 2.52 (2R).Preparation of aminoalcohol by dibenzylation: 2-Dibenzylamino-ethanol (Intermediate) To a vigorously stirred solution of 6.7 ml (1.12 mol, I equiv.) ethanolamine in 120 ml of (1/1) MeOH/H31) Preparation of aminoalcohols; a. By dibenzylation:; Preparation of 2-Dibenzylamino-ethanol (Intermediate):; To a vigorously stirred solution of 6.7 ml (1.12 mol, 1 equiv.) ethanolamine in 120 ml of (1/1) MeOH/HStep 1: Preparation of 2-(dibenzylamino)ethanol (Intermediate 31) To a solution of 2-aminoethanol (500 mg, 8.19 mmol) and TEA (2.74 mL, 19.7 mmol) in EtOH (11 mL) was added benzyl chloride (1.90 mL, 16.4 nimol) in EtOH (2.0 mL) at room temperature. The reaction mixture was refluxed for 12 hours.After evaporation of volatiles, the residue was diluted with diethyl ether. The mixture was extracted with diluted with diethyl ether and extracted with 2 N aq. HCI. The separated aqueous layer was neutralized with Na2CO3 and extracted with diethyl ether. The separated organic layer was dried over Na2SO4, filtered and concentrated in vacuo to obtain the title compound (980 mg, 50percent), which was used for the nextreaction without further purification.‘H-NMR (400 MHz, CDCI3): 7.36-7.15 (m, 1OH), 3.63 (s, 4H), 3.58 (t, J= 5.2 Hz, 2H), 2.67 (t, J= 5.2 Hz, 2H) * OH peak was not observed.Treat a mixture of 2-(benzylamino)ethanol (0.95 mL, 6.6 mmol) in ACN (35 mL) with potassium carbonate (1.83 g, 13.2 mmol) followed by benzyl bromide (1.18 mL, 9.89 mmol). Heat the reactions mixture at 80° C. for 1.5 hours. Cool the reaction to room temperature and filter the mixture. Concentrate the filtrate under reduced pressure and purify the residue by silica gel column chromatography eluting with a gradient from 0-30percent EtOAc in hexane to give the title compound 1.7 g (100percent). MS (m/z): 242 (M+1).Preparation Example: Preparation Acetic acid 2-dibenzylamino-ethyl ester; Stepi : 0.5 gram of dibenzylamine (2.5 mmol), 0.446 gram of ethylenecarbonate (5 mmol) and 0.215 gram of tetraethylammoniumiodide (083 mmol) were mixed together at room temperature. The solid mixture was then heated at 140

Molecular Weight:241.33
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:241.146664230
Monoisotopic Mass:241.146664230
Topological Polar Surface Area:23.5
Heavy Atom Count:18
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes