Ammonium Chloride → 4,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)dianiline

HRID 1470915Notes

Reaction equation

HRID 1470915 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.C1COCC1.O.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:22]2[CH:23]=[CH:24][C:25]([NH2:28])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 596168701-(4-Fluorophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

Product 1

HCID 596170274,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)dianiline

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product from Example 1D (0.501 g, 1.23 mmol) in ethanol (5 ml) and THF (5.00 ml) was added iron powder (0.412 g, 7.38 mmol) and a solution of ammonium chloride (0.197 g, 3.69 mmol) in water (1.0 ml). The resulting mixture was stirred at 80° C. for 45 min. The mixture was cooled, filtered through celite, washed with ethanol, and concentrated in vacuo. The crude product was purified by chromatography on silica gel using a solvent gradient of 0-100% ethyl acetate in hexanes to give the title compound as a mixture of cis and trans isomers (0.135 gm, 32%).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. washwashed with ethanol
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography on silica gel using a solvent gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c86b5ad6ca6d43b1829ddea12eda7e0e
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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