Acetic Acid → 3-chloro-N-[1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-4-fluorobenzenesulfonamide

To a stirred solution of 3-chloro-4-fluoro-N-[4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-benzenesulfonamide (0.0321 g, 0.04 mmol) in ClCH2CH2Cl (0.5 mL) at room temperature under Ar was added cyclopropanecarboxaldehyde (0.005 mL, 0.048 mmol, 1.2 eq) and HOAc (0.05 mL, 1%v/v). The mixture was stirred for 0.5 h. Na(OAc)3BH (0.015 g, 0.06 mmol, 1.5 eq) was added and the mixture stirred for 16 h, diluted with EtOAc (20 mL) and washed with saturated aqueous NaHCO3 solution (10 mL) and saturated brine (10 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated by rotary evaporation, then dried under high vacuum to give 3-chloro-N-[1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-4-fluorobenzenesulfonamide (0.047 g, 0.04 mmol, 95%). MS (ESI): 563.1/565.1 (M+1).

1. stirringthe mixture stirred for 16 h
2. washwashed with saturated aqueous NaHCO3 solution (10 mL) and saturated brine (10 mL)
3. dry with materialThe organic layer was dried over anhydrous Na2SO4
4. filtrationfiltered
5. concentrationconcentrated by rotary evaporation
6. customdried under high vacuum

ORD record

ord-c7388ea6e5b644a1b0cd4a68211b514d

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06887889B2