4-Fluorobenzaldehyde → N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

HRID 402513

반응식

HRID 402513 반응식
[F: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>C1(C)C=CC=CC=1>[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13][NH:14][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 680234-FluorobenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 11615438N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine수율 93.9%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

12.4 g of 4-fluorobenzaldehyde were dissolved in 100 mL of toluene and reacted with 10.5 g of 2-aminoacetaldehyde dimethylacetal and 1.90 g of p-toluenesulfonic acid monohydrate for two hours at a Dean Stark apparatus. The solution was allowed to cool down, extracted with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and evaporated to dryness. The crude product was dissolved in 100 mL of ethanol. 1.89 g of sodium borohydride were added portionwise. Stirring was continued overnight. For workup, acetic acid was added until no gas evolution could be observed. Then the solution was evaporated to dryness, taken up in dichloromethane and washed twice with water. The organic layer was extracted with brine, dried over magnesium sulfate and evaporated to dryness. The obtained crude product (20 g) was used for further reactions without purification. Rt=0.86 min (Method B). Detected mass: 182.1 (M-OMe−), 214.2 (M+H+).

후처리

  1. temperatureto cool down
  2. extractionextracted with saturated sodium bicarbonate solution, water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. dissolutionThe crude product was dissolved in 100 mL of ethanol
  6. addition1.89 g of sodium borohydride were added portionwise
  7. additionFor workup, acetic acid was added until no gas evolution
  8. customThen the solution was evaporated to dryness
  9. washwashed twice with water
  10. extractionThe organic layer was extracted with brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated to dryness

출처 및 근거

ORD 기록
ord-ac5936983d904b58a6644492d8696f1d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742116B2

연결된 노트

불러오는 중…