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

HRID 352217

반응식

HRID 352217 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-303afba746514b44a3842a117fd19d96
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743794B2

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