4-Bromobenzaldehyde → N-(4-Bromobenzyl)-2,2-dimethoxyethanamine

HRID 404714

반응식

HRID 404714 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13][NH2:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:14][CH2:13][CH:12]([O:15][CH3:16])[O:11][CH3:10])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 707414-BromobenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydride

생성물 1

HCID 59226241N-(4-Bromobenzyl)-2,2-dimethoxyethanamine수율 81.7%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매

실험 절차

50 g (270.2 mmol) 4-bromobenzaldehyde were dissolved in 200 ml of toluene and 28.4 g (270.2 mmol) aminoacetaldehyde dimethylacetal were added. After the addition of 5.1 g (27.0 mmol) p-toluenesulfonic acid monohydrate, the reaction mixture was heated under reflux in a Dean Stark apparatus. After 4 h, the reaction was cooled to room temperature and washed with saturated sodium hydrogen carbonate-solution (2×) and water. The combined aqueous layers were extracted with Toluene and the combined organic layers were dried over magnesium sulfate and evaporated. The residue was dissolved in 200 ml of ethanol and 5.11 g (135.1 mmol) of sodium borohydride were added in small portions. After stirring for 2 h at room temperature and standing overnight, 5.0 ml acetic acid were added and the solvent was removed i. vac. The residue was taken up in dichloromethane and washed (2×) with water. After drying over magnesium sulfate and evaporation, 60.5 g of the title compound were obtained (crude product), which were used without further purification. Rt=0.80 min (Method C). Detected mass: 274.1/276.1 (M+H+).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux in a Dean Stark apparatus
  3. washwashed with saturated sodium hydrogen carbonate-solution (2×) and water
  4. extractionThe combined aqueous layers were extracted with Toluene
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue was dissolved in 200 ml of ethanol
  8. waitstanding overnight
  9. customthe solvent was removed i
  10. washwashed (2×) with water
  11. dry with materialAfter drying over magnesium sulfate and evaporation

출처 및 근거

ORD 기록
ord-5d4402caa3d54c78a237de7453d9ab3a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748614B2

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