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

HRID 1775152Notes

Reaction equation

HRID 1775152 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>[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

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 739342,6-DifluoropyridineHCID 81531Diisopropylethylamine

Product 1

HCID 57619459(4-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amineYield 67.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To 2,6-difluoro-pyridine (20, 3.80 g, 33.0 mmol) in 20.0 mL ofN-methylpyrrolidone, 4-chloro-benzylamine (21, 5.6 mL, 46.0 mmol) and N,N-diisopropylethylamine (10.0 mL, 57.4 mmol) were added. The reaction was stirred at 90° C. overnight, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 25% ethyl acetate in hexane. Appropriate fractions were combined and the solvents removed under vacuum, and the resulting material was washed with ethyl acetate/hexane to provide the desired compound as a white solid (22, 5.30 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with 25% ethyl acetate in hexane
  7. customthe solvents removed under vacuum
  8. washthe resulting material was washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-b7388047cd2f492bb1794c7ddb3e5cd8
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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