Benzylamine → HCID 23206741, compound

Pentachloropyridine (80 g, 320 mmol) is treated with benzyl amine (104 mL, 96 mmol), dissolved in dioxane (1 L) and refluxed for 16 hours. The reaction mixture is cooled to ambient temperature and the precipitated white solid is removed by filtration. The filtrate is concentrated to a brown residue and triturated with 4% ethyl acetate in hexane (3×250 mL) to give 4-benzylamino-2,3,5,6-tetrachloropyridine as an off-white solid (40 g, 124 mmol). This material is dissolved in chloroform (400 mL), cooled in an ice bath and treated with trifluoroacetic acid (500 mL) and 30% hydrogen peroxide (100 mL). The reaction mixture is warmed to room temperature overnight and treated with additional trifluoroacetic acid (500 mL) and 30% hydrogen peroxide (100 mL). After stirring 24 hours the reaction is treated with water (1 L). The lower organic layer is separated and the aqueous layer is extracted with chloroform. The combined organic layers are concentrated to a solid residue and redissolved in ethyl acetate/hexane (30 mL). The suspended orange solid is removed and the filtrate is loaded on a silica flash column. The column is eluted with hexane and the title compound is collected as a white solid (15.6 g, 60 mmol). EI MS m/z 260, 262, 264 [M+].

1. temperaturerefluxed for 16 hours
2. customthe precipitated white solid is removed by filtration
3. concentrationThe filtrate is concentrated to a brown residue
4. customtriturated with 4% ethyl acetate in hexane (3×250 mL)

ORD record

ord-1378c578735445fea89405efa04f357b

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2