Triethylamine → (rac)-N-[1-(5-Bromo-pyridin-3-yl)-ethyl]-propionamide

HRID 1774852Notes

Reaction equation

HRID 1774852 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[Br:6][C:7]1[CH:8]=[C:9]([CH:13]([NH2:15])[CH3:14])[CH:10]=[N:11][CH:12]=1.CCN(CC)CC>C(Cl)Cl>[Br:6][C:7]1[CH:8]=[C:9]([CH:13]([NH:15][C:1](=[O:4])[CH2:2][CH3:3])[CH3:14])[CH:10]=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 710996741-(5-Bromopyridin-3-yl)ethan-1-amine

Product 1

HCID 89439879(rac)-N-[1-(5-Bromo-pyridin-3-yl)-ethyl]-propionamideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., propionyl chloride (138 mg, 1.5 mmol) was added dropwise to a solution of (rac)-1-(5-bromo-pyridin-3-yl)-ethylamine (201 mg, 1 mmol) and Et3N (153 mg, 1.5 mmol) in DCM (10 mL). The reaction mixture was stirred at room temperature for 1 hour before it was concentrated to dryness. The residue was redissolved in EtOAc and washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography to give the title compound (200 mg, 78%).

Workup

  1. concentrationwas concentrated to dryness
  2. dissolutionThe residue was redissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-b4ce180973d04490a28b06c64ad1ea69
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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