4-Fluoro-3-nitrobenzotrifluoride → N~1~-[3-(dimethylamino)propyl]-N~1~-methyl-4-(trifluoromethyl)benzene-1,2-diamine

HRID 883037Notes

Reaction equation

HRID 883037 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]([CH3:22])[CH2:17][CH2:18][CH2:19][NH:20][CH3:21].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:15][N:16]([CH3:22])[CH2:17][CH2:18][CH2:19][N:20]([CH3:21])[C:2]1[C:3]([NH2:12])=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 16109009N~1~-[3-(dimethylamino)propyl]-N~1~-methyl-4-(trifluoromethyl)benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was made using a procedure described in Collins, et. al., Tetrahedron, Vol. 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 N1,N1,N3-trimethylpropane-1,3-diamine (0.64 mL, 5.7 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. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8550aaa34ee14b31977a196afaae6f47
Source dataset
uspto-grants-2012_08
Patent number
US08236823B2

Reaction notes

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