1-[(Dimethylphosphoryl)methyl]-4-[4-nitro-2-(trifluoromethyl)benzyl]piperazine → 4-({4-[(Dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)aniline

HRID 1255949Notes

Reaction equation

HRID 1255949 reaction equation
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=2[C:22]([F:25])([F:24])[F:23])[CH2:8][CH2:7]1)([CH3:4])=[O:3]>C(O)C.[Pd]>[CH3:4][P:2]([CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=2[C:22]([F:25])([F:23])[F:24])[CH2:10][CH2:11]1)([CH3:1])=[O:3]

Participants

4

Reactant 1

HCID 577751371-[(Dimethylphosphoryl)methyl]-4-[4-nitro-2-(trifluoromethyl)benzyl]piperazine

Product 1

HCID 689121604-({4-[(Dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)anilineYield 161.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium (10 wt. %) on activated carbon (wet, 450 mg) was added to a solution of 1-[(dimethylphosphoryl)methyl]-4-[4-nitro-2-(trifluoromethyl)benzyl]piperazine (740 mg, 1.95 mmol) in 25 mL of ethyl alcohol. The reaction suspension was stirred under a hydrogen atmosphere (30 psi.) for 3 hours. The reaction mixture was then filtered through a short pad of celite. The celite pad was washed by 10 mL ethyl alcohol three times. The organic fractions were combined and evaporated to remove solvent and gave the desired compound as light yellow solid (1.10 g crude).

Workup

  1. filtrationThe reaction mixture was then filtered through a short pad of celite
  2. washThe celite pad was washed by 10 mL ethyl alcohol three times
  3. customevaporated
  4. customto remove solvent

Sources & evidence

ORD record
ord-03e81a1eb2e04ea188b7613aae516692
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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