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

HRID 82030

反応式

HRID 82030 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 17750321N-(3-Iodobenzyl)-N,N-dimethylamine収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f043558804914f0eaa1eb00ec10c1e75
出典データセット
uspto-grants-2014_09
特許番号
US08846712B2

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