2-Chloro-N,N-dimethylethylamine → Dimethyl-[2-(3-nitro-pyrrol-1-yl)-ethyl]amine

HRID 2409720Notes

Reaction equation

HRID 2409720 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:16][CH2:17][N:18]([CH3:20])[CH3:19]>CN(C=O)C>[CH3:19][N:18]([CH3:20])[CH2:17][CH2:16][N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5]1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 10796Cesium carbonateHCID 1458133-Nitropyrrole

Product 1

HCID 66914587Dimethyl-[2-(3-nitro-pyrrol-1-yl)-ethyl]amineYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-nitropyrrole (500 mg, 4.46 mmol), cesium carbonate (3.63 g, 11.2 mmol, 2.5 equiv), 1-chloro-2-dimethylaminoethane (835 mg, 5.8 mmol, 1.3 equiv) and DMF (5 mL) was stirred for 16 h at rt. The reaction mixture was quenched by addition of a saturated aqueous solution of NaHCO3 and extracted with DCM/MeOH (9:1, v/v). The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM→DCM/MeOH, 97:3) to afford 656 mg of the title compound as a yellow oil. Title compound: ESI-MS: 184.1 [M+H]+; TLC: Rf=0.38 (DCM/MeOH, 9:1).

Workup

  1. customThe reaction mixture was quenched by addition of a saturated aqueous solution of NaHCO3
  2. extractionextracted with DCM/MeOH (9:1
  3. washThe organic phase was washed with a saturated aqueous solution of NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (DCM→DCM/MeOH, 97:3)

Sources & evidence

ORD record
ord-7bebf7b6664b43b493d1165cb04feb03
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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