1-Methylpiperazine → 2-(4-Methylpiperazin-1-yl)-5-(trifluoromethyl)aniline

HRID 446244Notes

Reaction equation

HRID 446244 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-])=O.[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[NH2:12])[CH2:18][CH2:17]1

Participants

5

Reactant 3

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

Product 1

HCID 6932882-(4-Methylpiperazin-1-yl)-5-(trifluoromethyl)aniline

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-52b87f445c3b4af18f080abb742c95e7
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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