Triethylamine → HCID 19101711, compound

HRID 1974640Notes

Reaction equation

HRID 1974640 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([F:11])[C:5]([F:12])=[C:4](F)[C:3]=1[F:14].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C>O>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:4]2[C:5]([F:12])=[C:6]([F:11])[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[C:3]=2[F:14])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 70154Pentafluoronitrobenzene

Product 1

HCID 19101711HCID 19101711, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pentafluoronitrobenzene (10 g, 46.9 mmol) is cooled to 0° C. and treated dropwise with 1-methylpiperazine (5.2 ml, 47 mmol) in triethylamine (14 ml, 94 mmol). After 30 minutes at 0° C., the reaction mixture is allowed to reach room temperature. After one hour, the orange suspension is diluted with water (100 ml) and extracted with ether (3×100 ml). The combined organic layers are washed with saturated aqueous sodium chloride solution (100 ml), dried with magnesium sulfate and evaporated. Recrystallization from n-hexane-ether (1:1) yields 10 g of 1-methyl-4-(2,3,5,6-tetrafluoro-4-nitrophenyl)piperazine as red-brown crystals (73%): mp: 77°-78° C.; NMR(CDCl3):2.35(s,3H),2.54 (m,4H),3.44(m,4H).

Workup

  1. customto reach room temperature
  2. waitAfter one hour
  3. extractionextracted with ether (3×100 ml)
  4. washThe combined organic layers are washed with saturated aqueous sodium chloride solution (100 ml)
  5. dry with materialdried with magnesium sulfate
  6. customevaporated
  7. customRecrystallization from n-hexane-ether (1:1)

Sources & evidence

ORD record
ord-14c7cfd3d7224951a5388148b6063882
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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