1-Methylpiperazine → 1-Methyl-4-[2-nitro-4-(trifluoromethyl)phenyl]piperazine

HRID 1361587Notes

Reaction equation

HRID 1361587 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 28607241-Methyl-4-[2-nitro-4-(trifluoromethyl)phenyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Example 18 was prepared in accordance to a procedure described in Collins, et. al., Tetrahedron, 48, No. 37, pp 7887-7898, 1992. To a solution of 1-Fluoro-2-nitro-4-trifluoromethyl-benzene (1.0 g, 4.78 mmol) in dry THF (24 mL) was added 1-Methyl-piperazine (0.64 mL, 5.74 mmol). The solution turned bright yellow. NaHCO3 (1.1 g, 13 mmol) was added and the reaction was stirred at room temperature and monitored by LCMS: The reaction was filtered and concentrated before being taken up in CH2Cl2 and H2O. The organic layer was separated, dried with MgSO4, filtered, and concentrated to afford the title compound as an orange-brown oil.

Workup

  1. customExample 18 was prepared in accordance to a procedure
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customThe organic layer was separated
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a288a3ca3714433b87346caedd679ce0
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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