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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 922839Generated: October 27, 2026

Acetic Acid → 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((dimethylamino)methyl)benzamide

https://huagongshe.com/reaction/922839

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantFormaldehydeHCID 712—
ReactantDimethylformamideHCID 6228—
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(aminomethyl)benzamideHCID 66877029—
Product2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((dimethylamino)methyl)benzamideHCID 44252148—

Reaction Steps

2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(aminomethyl)benzamide (80 mg, 0.20 mmol) was dissolved in DMF (5 mL) and treated with AcOH (10 uL), paraformaldehyde (43 mg, 0.47 mmol), and sodium triacetoxyborohydride (125 mg, 0.59 mmol). After stirring for 16 h, the solvent was evaporated and the residue was dissolved in ethyl acetate. The organic layer was washed with 1 N Sodium hydroxide, dried (MgSO4) and concentrated. The crude product was purified by reverse phase HPLC to produce 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((dimethylamino)methyl)benzamide. MS (Q1) 400.0 (M)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278961B2
Source datasetuspto-grants-2016_03
ORD IDord-c4b76dd4dc604b138e4dfdb6960950b1
Source noteuspto-grants-2016_03