Triethylamine → Ethyl 2-(dimethylamino)-2-(pyridin-3-yl)acetate

HRID 352217

Reaction equation

HRID 352217 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5](Br)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].Cl.[CH3:15][NH:16][CH3:17].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([N:16]([CH3:17])[CH3:15])[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetate

Product 1

HCID 69849128Ethyl 2-(dimethylamino)-2-(pyridin-3-yl)acetateYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromopyridin-3-yl-acetic acid ethyl ester (2.54 g; 10.2 mmol) was reacted in a sealed tube, at rt., in CH2Cl2, overnight with N,N-dimethylamine hydrochloride (3.34 g; 41.0 mmol; 4 equiv) and Et3N (5.8 mL; 41.0 mmol; 4 equiv). The reaction solution was evaporated to dryness, dissolved in CH2Cl2, washed five times with saturated NaHCO3 (aq), washed once with saturated NaCl (aq), dried with Na2SO4, filtered, and concentrated in vacuo. The resulting brown oil was purified with silica gel chromatography in a 3×25 cm glass column using a 0.5% methanol/chloroform (v/v) mobile phase. The desired product was isolated as a yellow oil (1.12 g; 53% yield). MS(ES) calc'd: [M+H]+=208.1 m/z. Found: 208.1 m/z.

Workup

  1. customovernight
  2. customThe reaction solution was evaporated to dryness
  3. dissolutiondissolved in CH2Cl2
  4. washwashed five times with saturated NaHCO3 (aq)
  5. washwashed once with saturated NaCl (aq)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting brown oil was purified with silica gel chromatography in a 3×25 cm glass column

Sources & evidence

ORD record
ord-303afba746514b44a3842a117fd19d96
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

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