Water → (4-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine

HRID 1024242Notes

Reaction equation

HRID 1024242 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C.O>CN1CCCC1=O>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 660364-ChlorobenzylamineHCID 739342,6-DifluoropyridineHCID 81531Diisopropylethylamine

Product 1

HCID 57619459(4-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To 2,6-difluoropyridine (58, 9.85 g, 0.0856 mol) in N-methylpyrrolidinone (50.0 mL) were added p-chlorobenzylamine (61, 10.5 mL, 8.63 mmol) and N,N-diisopropylethylamine (30.0 mL, 0.172 mol). The reaction was stirred at 90° C. overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 25% ethyl acetate in hexane, then washed with ethyl acetate/hexane to give a white solid (536, 10 g, 50%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 25% ethyl acetate in hexane
  7. washwashed with ethyl acetate/hexane
  8. customto give a white solid (536, 10 g, 50%)

Sources & evidence

ORD record
ord-3adb3c860ee94c48bcea71e8da8dcdf4
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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