2-[(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridi

To 10 mL of DMF were added 0.5 g of gentisic acid, 0.68 g of EDC, 0.48 g of HOBt, 1.4 mL of TEA and 1.08 g of 2-[(4-chlorophenyl)(4- and the mixture was stirred at 60 to 80C for 4 hours. 10 mL of EtOAc and 10 mL of purified water were added to the reaction mixture and the layers were separated. The aqueous layer was extracted once with 10 mL of EtOAc and the aqueous layer was discarded. The organic layer was washed three times with 10 mL of purified water, dried over Na2SO4 and filtered. The filtrate was distilled under reduced pressure and purified by flash column chromatography to obtain 0.78 g of the title compound as a foam. Yield: 54.9% 1H NMR(400MHz, DMSO-d6) 9.05(s, 1H), 8.89(s, 1H), 8.47(dd, J=0.8 and 4.0, 1H), 7.81(td, J=1.6 and 8.0, 1H), 7.57(d, J=7.6, 1H), 7.43'7.25(m, 5H), 6.67'6.60(m, 2H), 6.46(d, J=2.8, 1H), 5.69(s, 1H), 3.93(brs, 1H), 3.64(p, J=4.4, 1H), 3.14(brs, 2H), 1.85(brs, 1H), 1.55'1.52(m, 2H)To 10 mL of DMF were added 0.5 g of vanillic acid, 0.51 g of EDC, 0.44 g of HOBt, 1.44 mL of TEA and 0.99 g of 0.5 g of 3, 4-diacetoxybenzoic acid obtained in Preparation was added to DCM 10 mL, and the mixture was stirred at 10C. 0.66 g of PCl5 was added at 10C or lower, the mixture was stirred for 2 hours while maintaining the temperature at 0 to 10C, and 10 ml of purified water was added for layer separation. The aqueous aqueous layer was discarded and the organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated, added with 10 mL of DCM, cooled to 0C, and 0.57 g of The 30.3 g (100 mmol, 1.0 eq) racemate into 1 L three flasks, adding 240 ml acetone, stirring at the room temperature, the solid is not completely soluble. Take another (S)- binaphthol phosphate 36.6 g (100 mmol, 1 . 05 eq) is placed on the 250 ml single-port in the bottle, add 40 ml N, N - dimethyl formamide, water bath 45 C stirring, the solution is clarified, then the solution is dropped in the suspension liquid to acetone, about 10 minutes after adding, then heating to reflux, under reflux conditions to clarify the solution gradually, then with a white solid precipitated. Return 1 h after cooling, filtering, 40 ml acetone washing, 40 - 50 C vacuum drying 2 h, get white powder 26.0 g, yield 40%.To 61.3 (0.202 mol) g4 - [(4-chlorophenyl) (2-pyridyl) methoxy] piperidineWas added 400 ml of ethanol, Fumaric acid (depending on the amount of fumaric acid added, respectively, as 1-5 groups, the specific amount of added and the amount of added substances in the table4), heating the reaction system to 55-60 C, stirring at that temperature for 1 hrs, then cooling to room temperature and stirring overnight, A solid precipitation, the system placed in ice water bath and then continue stirring 5hrs, filter, filter cake with 50mlx3 cold ethanol foam wash, dryDry after4 - [(4-chlorophenyl) (2-pyridyl) methoxy] piperidine fumaric acidThe crude salt was a yellow solid.4.542kg

Molecular Weight:302.8
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:302.1185909
Monoisotopic Mass:302.1185909
Topological Polar Surface Area:34.2
Heavy Atom Count:21
Complexity:301
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes