4-Isopropylaniline → N-(4-(Dimethylamino)benzyl)-4-isopropylbenzenamine

HRID 33769

반응식

HRID 33769 반응식
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH:12]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([CH3:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[Cl-].CCOC(C)=O>C1COCC1>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:19][C:18]2[CH:20]=[CH:21][C:15]([CH:12]([CH3:14])[CH3:13])=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 74644-IsopropylanilineHCID 74794-(Dimethylamino)BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86583716Ammonium chloride ethyl acetate

생성물 1

HCID 21957887N-(4-(Dimethylamino)benzyl)-4-isopropylbenzenamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 0.33 M solution of 4-(dimethylamino)benzaldehyde in THF at 0° C. was added 1.1 equiv of 4-isopropylaniline followed by 1.5 equiv of sodium triacetoxyborohydride. After allowing the reaction to warm to room temperature overnight, this mixture was poured into a separatory funnel containing aqueous NH4Cl/EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude material was further purified by flash chromatography, eluting with a gradient from 100% hexanes to 10% EtOAc/hexanes to provide the title compound as a white solid.

후처리

  1. customthe reaction
  2. additionthis mixture was poured into a separatory funnel
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was further purified by flash chromatography
  8. washeluting with a gradient from 100% hexanes to 10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-c2f206464e554652baed0836d7fe1452
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429666B2

연결된 노트

불러오는 중…