Acetonitrile → HCID 6500399, compound

HRID 2241912Notes

Reaction equation

HRID 2241912 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C.C(#N)C>[Pt].CO>[N:15]1([C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 949542-Fluoro-5-nitrobenzotrifluoride

Product 1

HCID 6500399HCID 6500399, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-fluoro-4-nitro-2-(trifluoromethyl)benzene (1.05 g, 5.00 mmol), piperidine (0.592 ml, 6.00 mmol), diisopropylethylamine (1.31 ml, 7.50 mmol) and acetonitrile (10 ml) was refluxed for 8 hours. Methanol (10 ml) and 10% platinum on activated carbon (0.10 g) were added to the residue obtained by evaporation of the solvent of the reaction mixture under reduced pressure, and the mixture was stirred at room temperature for 12 hours under hydrogen atmosphere. The reaction mixture was filtered through celite. The residue obtained by concentration of the filtrate under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (1.11 g, 91%) as a colorless liquid.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customobtained by evaporation of the solvent of the reaction mixture under reduced pressure
  3. filtrationThe reaction mixture was filtered through celite
  4. customThe residue obtained by concentration of the filtrate under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c1d37dfdf6dd4e8da58f4add32c6719b
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

Loading…