N,N-dimethyl-p-phenylenediamine → N4-Heptyl-N1,N1-dimethyl-1,4-benzenediamine

HRID 1457599노트

반응식

HRID 1457599 반응식
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 8130HeptanalHCID 516892Sodium BicarbonateHCID 2724942Triacetoxyborohydride

생성물 1

HCID 22099398N4-Heptyl-N1,N1-dimethyl-1,4-benzenediamine수율 46.8%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 3.50 g of N,N-dimethyl-p-phenylenediamine, 4.592 g of heptanal, 9.095 g of triacetoxyborohydride, 1.841 g of acetic acid and 257 ml of dichloromethane was stirred at room temperature for one hour. A saturated sodium hydrogen carbonate solution is added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue obtained was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1) to give 2.819 g of N,N-dimethyl-N'-heptyl-p-phenylenediamine (yield: 39%, oily product, IR (film): 3375, 2927, 1519 cm-1).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-a456221f39354a91800f7687886e9831
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849732

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