4-Fluorobenzaldehyde → N-(3,5-Dichlorobenzyl)-N-(4-fluorobenzyl)-3-((4-fluorobenzylamino)methyl)benzenesulfonamide

To a solution of 3-(aminomethyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzenesulfonamide (290 mg, 0.64 mmol) in CH2Cl2 (6 mL) was added 4-fluorobenzaldehyde (0.07 mL, 0.64 mmol). The resulting mixture was stirred at rt. for 1 h. To the mixture was added sodium triacetoxyborohydride (217 mg, 1.02 mmol) under N2 atmosphere. The resulting mixture was stirred at rt for 20 h. To the reaction mixture was added saturated aq NaHCO3 solution and the mixture was stirred for 20 minutes. The mixture was concentrated. The residue was diluted with ethyl acetate and saturated aq NaHCO3 solution. The organic layer was washed with brine and dried over MgSO4. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel eluting with 100% CH2Cl2 to 25% ethyl acetate in CH2Cl2 to obtain the desired product as a colorless oil (0.16 g, 45%). 1H NMR (CDCl3): δ 7.86 (s, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.65 (d, J=8.0 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 7.33-7.29 (m, 2H), 7.16-7.15 (m, 1H), 7.09-6.99 (m, 4H), 6.94-6.89 (m, 2H), 6.85-6.84 (m, 2H), 4.32 (s, 2H), 4.25 (s, 2H), 3.89 (s, 2H), 3.78 (s, 2H), 1.77 (bs, 1H); MS (ESI): [M+H]+=561.0.

1. stirringThe resulting mixture was stirred at rt for 20 h
2. stirringthe mixture was stirred for 20 minutes
3. concentrationThe mixture was concentrated
4. additionThe residue was diluted with ethyl acetate and saturated aq NaHCO3 solution
5. washThe organic layer was washed with brine
6. dry with materialdried over MgSO4
7. concentrationThe filtrate was concentrated
8. customthe residue was purified by flash chromatography on silica gel eluting with 100% CH2Cl2 to 25% ethyl acetate in CH2Cl2

ORD record

ord-72d8f7878364466eb7416542bab7153e

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501992B2