3-[5-(7-azabicyclo[2.2.1]heptan-7-yl)-2-nitro-phenyl]-N,N-dimethyl-prop-2-yn-1-amine → 4-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-(3-(dimethylamino)prop-1-ynyl)aniline

HRID 1908224Notes

Reaction equation

HRID 1908224 reaction equation
[CH:1]12[N:7]([C:8]3[CH:9]=[CH:10][C:11]([N+:20]([O-])=O)=[C:12]([C:14]#[C:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:13]=3)[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2>O.[Fe]>[CH:1]12[N:7]([C:8]3[CH:9]=[CH:10][C:11]([NH2:20])=[C:12]([C:14]#[C:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:13]=3)[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2

Participants

4

Reactant 1

HCID 584786333-[5-(7-azabicyclo[2.2.1]heptan-7-yl)-2-nitro-phenyl]-N,N-dimethyl-prop-2-yn-1-amine

Product 1

HCID 575168474-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-(3-(dimethylamino)prop-1-ynyl)anilineYield 48.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

3-[5-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-nitro-phenyl]-N,N-dimethyl-prop-2-yn-1-amine 26 (340 mg, 1.14 mmol), iron (634 mg, 11.36 mmol) and ferrous sulfate heptahydrate (316 mg, 1.136 mmol) were suspended in water (1 mL) and refluxed for 20 min. The reaction was filtered and the solid washed with methanol and dichloromethane. The filtrate was concentrated and purified by silica gel chromatography using (0-5% methanol in dichloromethane) to provide 4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(3-dimethylaminoprop-1-ynyl)aniline 27 (148 mg, 48% yield). LC/MS m/z 270.3 [M+H]+, retention time 0.25 min (RP-C18, 10-99% CH3CN/0.05% TFA over 3 min).

Workup

  1. temperaturerefluxed for 20 min
  2. filtrationThe reaction was filtered
  3. washthe solid washed with methanol and dichloromethane
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c67d5beac69f478f8b93f9d5f27ca01e
Source dataset
uspto-grants-2013_12
Patent number
US08598205B2

Reaction notes

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