Aniline → 2,5-Bis(4-nitrophenyl)-1-phenylpyrrolidine

HRID 2364777Notes

Reaction equation

HRID 2364777 reaction equation
CS(O[CH:6]([C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=O)=O.[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[CH2:8][CH2:7][CH:6]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)[N:33]2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

3

Reactant 2

HCID 6115AnilineHCID 596171791,4-Bis(4-nitrophenyl)butane-1,4-diyl dimethanesulfonate

Product 1

HCID 866490982,5-Bis(4-nitrophenyl)-1-phenylpyrrolidine

Procedure

A mixture of the product from Example 1C (50 mg, 0.102 mmol) and aniline (0.2 ml, 2.19 mmol) were stirred at rt for 48 h. The mixture was partitioned between 1N aq. HCl and ethyl acetate, and the organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-50% ethyl acetate in hexanes. The title compound was obtained as a yellow solid (19 mg, 48%).

Workup

  1. customThe mixture was partitioned between 1N aq. HCl and ethyl acetate
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ecc97388647e4325be01b7151d134ea1
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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