Ethanol → 4,4'-(1-(4-(6-(Dimethylamino)pyridin-3-yl)phenyl)pyrrolidine-2,5-diyl)dianiline

HRID 2364826Notes

Reaction equation

HRID 2364826 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[N:11]2[C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[CH:32][C:33]([N:36]([CH3:38])[CH3:37])=[N:34][CH:35]=3)=[CH:26][CH:25]=2)=[CH:6][CH:5]=1)([O-])=O.C(O)C>C1COCC1.[Pt](=O)=O>[CH3:37][N:36]([CH3:38])[C:33]1[N:34]=[CH:35][C:30]([C:27]2[CH:26]=[CH:25][C:24]([N:11]3[CH:12]([C:15]4[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=4)[CH2:13][CH2:14][CH:10]3[C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=3)=[CH:29][CH:28]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 866491085-(4-(2,5-bis(4-nitrophenyl)pyrrolidin-1-yl)phenyl)-N,N-dimethylpyridin-2-amine

Product 1

HCID 672370304,4'-(1-(4-(6-(Dimethylamino)pyridin-3-yl)phenyl)pyrrolidine-2,5-diyl)dianiline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 99A (26.8 mg, 0.053 mmole) was dissolved in THF (526A) in a round bottom flask to which was subsequently added ethanol (526 μL) resulting in a yellow precipitate. To this suspension was added platinum (IV) oxide (3.16 mg, 0.014 mmole). The flask was capped with a septum and the contents vacuum degassed three times. Hydrogen was introduced via a balloon and the mixture allowed to stir at room temperature for two and one half hours. The reaction mixture was vacuum filtered through a sand and celite plug, which was rinsed with THF and methanol until the filtrate was u.v.(−). The filtrate was concentrated in vacuo to provide the title compound in quantitative yield as a white solid as a mixture of stereoisomers. MS ESI(+), m/z @ 450.7 (M+H)+.

Workup

  1. customresulting in a yellow precipitate
  2. customThe flask was capped with a septum
  3. customthe contents vacuum degassed three times
  4. additionHydrogen was introduced via a balloon
  5. filtrationfiltered through a sand and celite plug, which
  6. washwas rinsed with THF and methanol until the filtrate
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-860de0c324da437c8b74ec0ac2fe8e8e
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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