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 383401Notes

Reaction equation

HRID 383401 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>C(O)(=O)C.O.CO.[Zn]>[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

6

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 30%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-[5-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-nitro-phenyl]-N,N-dimethyl-prop-2-yn-1-amine (75 mg, 0.25 mmol) was dissolved in a mixture of glacial acetic acid (940 μL) and water (230 μL). Zn dust (164 mg, 2.51 mmol) was added at room temperature. The solution was stirred for 10 min. The reaction was diluted with methanol (5 mL), filtered and concentrated. The residue was dissolved in ethyl acetate, washed with 50% saturated NaHCO3 (2×20 mL) and brine, dried over Na2SO4, filtered, and dried down to a light orange solid. Purification by silica gel chromatography (5-15% methanol/dichloromethane) provided 4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(3-(dimethylamino)prop-1-ynyl)aniline as a light orange oil (20 mg, 30% yield). LC/MS m/z 270.5 [M+H]+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 50% saturated NaHCO3 (2×20 mL) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customdried down to a light orange solid
  8. customPurification by silica gel chromatography (5-15% methanol/dichloromethane)

Sources & evidence

ORD record
ord-8774c080d07d4e22be8c83bf7b47952a
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

Loading…