N,N,N'-Trimethyl-N'-(2-nitro-4-pentafluoroethyl-phenyl)-propane-1,3-diamine → HCID 59428005, compound

HRID 1361583Notes

Reaction equation

HRID 1361583 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][CH2:5][N:6]([CH3:23])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[N+:20]([O-])=O.[H][H]>CO.[Pd]>[CH3:24][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]([CH3:23])[C:7]1[C:8]([NH2:20])=[CH:9][C:10]([C:13]([F:19])([F:18])[C:14]([F:15])([F:16])[F:17])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 86602588N,N,N'-Trimethyl-N'-(2-nitro-4-pentafluoroethyl-phenyl)-propane-1,3-diamineHCID 178418361HCID 178418361, compound

Product 1

HCID 59428005HCID 59428005, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N,N, N′-Trimethyl-N′-(2-nitro-4-pentafluoroethyl-phenyl)-propane-1,3-diamine (Step 2, 800 mg, 2.25 mmol) was dissolved in 15 mL MeOH. Palladium (120 mg, 0.307 mmol, 10% w/w on carbon) was added, a balloon containing hydrogen was inserted, and the reaction was stirred at RT for 18 h. The solution was then filtered through a pad of Celite and concentrated, yielding viscous brown oil. The crude mixture was purified using reverse phase chromatography to give the title compound as reddish-brown oil. MS (M+H)+=326; Calc'd 325.32 for C14H20F5N3.

Workup

  1. filtrationThe solution was then filtered through a pad of Celite
  2. concentrationconcentrated
  3. customyielding viscous brown oil
  4. customThe crude mixture was purified

Sources & evidence

ORD record
ord-23f03752eb8b40f1a5d342f16bf82285
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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