Cyclopropylamine → HCID 19101702, compound

HRID 1974641Notes

Reaction equation

HRID 1974641 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([F:14])=[C:12](F)[C:11]([N+:16]([O-:18])=[O:17])=[C:10]([F:19])[C:9]=2[F:20])[CH2:4][CH2:3]1.[CH:21]1([NH2:24])[CH2:23][CH2:22]1>C(N(CC)CC)C>[CH:21]1([NH:24][C:12]2[C:11]([N+:16]([O-:18])=[O:17])=[C:10]([F:19])[C:9]([F:20])=[C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[C:13]=2[F:14])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 19101711HCID 19101711, compound

Product 1

HCID 19101702HCID 19101702, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1-Methyl-4-(2,3,5,6-tetrafluoro-4-nitrophenyl)piperazine(9.4 g,34.15 mmol) is suspended in triethylamine (20 ml) and treated dropwise with cyclopropylamine (2.9 ml, 41 mmol). During the addition, the temperature is maintained below +10° C. The reaction mixture is stirred at room temperature overnight, then evaporated, suspended in ether (200 ml) and sequentially washed with 1N aqueous sodium hydroxide solution (45 ml), saturated aqueous sodium chloride solution, then dried (magnesium sulfate) and evaporated. Recrystallization from n-hexane yields 9.7 g of N-cyclopropyl-2,4,5-trifluoro-3-(4-methyl-1-piperazinyl)-6-nitroaniline as orange crystals (86%): mp:75° C.; NMR (CDCl3): 0.55 (m,2H),0.75(m,2H),2.35(s,3H),2.53(m,4H),2.92(m,1H),3.40(m,4H), 6.65(s,1H).

Workup

  1. additionDuring the addition
  2. temperaturethe temperature is maintained below +10° C
  3. customevaporated
  4. washsequentially washed with 1N aqueous sodium hydroxide solution (45 ml), saturated aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-af0c9114ab214f20a87f235bb6ab8f58
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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