Triethylamine → (3S,5S)-1-(3-Amino-4-nitrophenyl)-N,N,5-trimethyl-3-pyrrolidinamine

HRID 1988963Notes

Reaction equation

HRID 1988963 reaction equation
[CH3:1][N:2]([CH3:9])[C@@H:3]1[CH2:7][NH:6][C@@H:5]([CH3:8])[CH2:4]1.[NH2:10][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13](F)[CH:12]=1.CCN(CC)CC>CN1CCCC1=O.O>[CH3:1][N:2]([CH3:9])[C@@H:3]1[CH2:7][N:6]([C:13]2[CH:12]=[C:11]([NH2:10])[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=2)[C@@H:5]([CH3:8])[CH2:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 753995-Fluoro-2-nitroanilineHCID 45087348HCID 45087348, compound

Product 1

HCID 58650611(3S,5S)-1-(3-Amino-4-nitrophenyl)-N,N,5-trimethyl-3-pyrrolidinamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

(2S,4S)-4-dimethylamino-2-methylpyrrolidine (1.0 equivalent) and 1-amino-3-fluoro-6-nitrobenzene(1.2 equivalents) were dissolved in N-methylpyrrolidinone, and Et3N(5.0 equivalents) was added. The solution was heated for 5 hours at 100° C. The solution was then cooled and diluted with water. The aqueous layer was extracted with ethyl acetate. The organic layer was then washed twice with H2O, once with brine, dried over Na2SO4, filtered, and concentrated. The crude material was purified by column chromatography (1:1 ethyl acetate:hexane to 1:20 MeOH:ethyl acetate to 1:1 MeOH:ethyl acetate to give the title compound as a yellow gum. LC/MS (m/z) 265.2 (MH+), Rt 1.65 minutes.

Workup

  1. temperatureThe solution was then cooled
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was then washed twice with H2O, once with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography (1:1 ethyl acetate

Sources & evidence

ORD record
ord-7c85f649cbdf4734921b4b34fadf2af5
Source dataset
uspto-grants-2010_01
Patent number
US07642278B2

Reaction notes

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