Cyclohexylamine → HCID 55067914, compound

HRID 243135Notes

Reaction equation

HRID 243135 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(#N)C>[CH:12]1([NH:18][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 679672,4-DifluoronitrobenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 55067914HCID 55067914, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,4-Difluoronitrobenzene (2.00 g, 12.57 mmol) was dissolved in acetonitrile (20 mL) and cyclohexylamine (1.25 g, 12.57 mmol) and DIPEA (2.2 mL, 12.57 mmol) added. The reaction mixture was stirred at RT overnight. The resultant mixture was concentrated in vacuo to afford a bright yellow gum. This was purified by column chromatography (silica gel, gradient 0-10% EtOAc in cyclohexane) to afford the title compound as a bright yellow oil (2.4 g, 92%). 1H NMR (CDCl3, 400 MHz): δ 8.20 (1H, dd, J=9.50, 6.22 Hz), 6.49 (1H, dd, J=11.75, 2.62 Hz), 6.31 (1H, ddd, J=9.51, 7.26, 2.61 Hz), 3.47-3.33 (1H, m), 2.11-1.98 (2H, m), 1.85-1.77 (2H, m), 1.72-1.60 (1H, m), 1.48-1.26 (5H, m)

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. customto afford a bright yellow gum
  3. customThis was purified by column chromatography (silica gel, gradient 0-10% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-be88972eabd44d2bb13308caf47b29a7
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…