Methyl iodide → 2-(1-Methylpiperidin-3-yl)-5-(trifluoromethyl)benzenamine

HRID 1042686Notes

Reaction equation

HRID 1042686 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)([O-])=O.I[CH3:21]>CC(C)=O.C1C=CC=CC=1.CO.[Pt](=O)=O>[CH3:21][N:16]1[CH2:17][CH2:18][CH2:19][CH:14]([C:5]2[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:4]=2[NH2:1])[CH2:15]1

Participants

7

Reactant 2

HCID 6328Methyl iodideHCID 463167623-(2-Nitro-4-(trifluoromethyl)phenyl)pyridine

Product 1

HCID 587119192-(1-Methylpiperidin-3-yl)-5-(trifluoromethyl)benzenamine

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 180AcetoneSolventHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To an orange solution of 3-(2-nitro-4-(trifluoromethyl)phenyl)pyridine (1.4 g, 5.2 mmol) in 2 ml acetone and 1 mL benzene was added iodomethane (1.0 ml, 16 mmol). The solution was allowed to stand for 5 days, and was concentrated in vacuo to give an orange solid. A portion of this material was treated with platinum (IV) oxide (0.11 g, 0.49 mmol) in 5 ml MeOH under an atmosphere of hydrogen for approximately 24 h. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Purification by silica gel chromatography (MC/MeOH/conc. NH4OH) provided the title compound. MS (m/z): 259.0 (M+H)+. Calc'd for C13H17P3N2: 258.28.

Workup

  1. concentrationwas concentrated in vacuo
  2. customto give an orange solid
  3. customThe reaction was flushed with nitrogen
  4. filtrationfiltered through celite
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (MC/MeOH/conc. NH4OH)

Sources & evidence

ORD record
ord-000fff290ab141238a506460310a9555
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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