Acetic Acid → N-(3-Iodobenzyl)-N,N-dimethylamine

HRID 82030

반응식

HRID 82030 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)C.[CH3:14][N:15](C)[C:16](=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:15]([CH3:16])[CH3:14]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 31374DimethylacetamideHCID 2526103-IodobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 17750321N-(3-Iodobenzyl)-N,N-dimethylamine수율 90%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a cold (0° C.) solution of 3-iodo-benzaldehyde (3 g, 12.9 mmol) in anhydrous dichloromethane (130 ml) were added acetic acid (1.9 ml) and N,N-dimethylacetamide. The yellow solution is stirred 10 minutes at 0° C. and sodium triacetoxyborohydride (6.85 g, 32.33 mmoles) is added by portions. The resulting mixture is stirred at room temperature for 90 minutes and evaporated to dryness under reduced pressure. Ethyl acetate and a saturated aqueous hydrogen carbonate solution were added to the residue and the two layers were separated The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to yield (3-iodo-benzyl)-dimethyl-amine (3.05 g, 90%) as a brown oil.

후처리

  1. stirringThe resulting mixture is stirred at room temperature for 90 minutes
  2. customevaporated to dryness under reduced pressure
  3. additionEthyl acetate and a saturated aqueous hydrogen carbonate solution were added to the residue
  4. customthe two layers were separated The organic phase
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-f043558804914f0eaa1eb00ec10c1e75
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846712B2

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