1-Methylpiperazine → 1-Methyl-4-(5-nitro-2-pentafluoroethyl-benzyl)-piperazine

HRID 887535Notes

Reaction equation

HRID 887535 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:2][C:3]2[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=2[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 219593672-Bromomethyl-4-nitro-1-pentafluoroethyl-benzene

Product 1

HCID 222492671-Methyl-4-(5-nitro-2-pentafluoroethyl-benzyl)-piperazine

Procedure

2-Bromomethyl-4-nitro-1-pentafluoroethyl-benzene (2.6 g) was added to N-methylpiperazine (5 ml) and stirred at RT for 3 h. The mixture was filtered and the filtrate was treated with 1-chlorobutane, extracted with 2N HCl (100 ml). The acidic solution was treated with 5N NaOH (6 ml) then extracted with EtOAc. The organic layer was removed, dried over MgSO4 and concentrated to give the compound as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was treated with 1-chlorobutane
  3. extractionextracted with 2N HCl (100 ml)
  4. additionThe acidic solution was treated with 5N NaOH (6 ml)
  5. extractionthen extracted with EtOAc
  6. customThe organic layer was removed
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e197ae56a1c5421d917b1a6561e1c11d
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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