Benzylamine → N-benzyl-(1-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine

HRID 2299653노트

반응식

HRID 2299653 반응식
CO[C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.C=CCC[C:18](=[O:21])CC.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:22]([NH:29][CH:10]1[CH2:9][CH2:8][CH2:7][C:6]2[C:12]([O:21][CH3:18])=[CH:13][CH:3]=[CH:4][C:5]=2[CH2:11]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 867587133-Methoxy-6,7,8,9-tetrahydrobenzocyclohepten hepten-5-one

생성물 1

HCID 18007167N-benzyl-(1-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 3-methoxy-6,7,8,9-tetrahydrobenzocyclohepten-hepten-5-one (6.0 g) and benzylamine (3.4 ml) in toluene (60 ml) in the presence of a catalytic amount of p-toluenesulfonic acid monohydrate was refluxed for 2 hours to remove water at the toluene azeotrope, and then the mixture was evaporated in vacuo. To the residue in methanol (60 ml) was added sodium borohydride (1.2 g) under nitrogen at 5° C., and the mixture was stirred at room temperature for 12 hours. The resulting mixture was poured into ice-cold water and stirred for 30 minutes. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate-methanol) over silica gel to afford N-benzyl-(1-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (7.27 g).

후처리

  1. customto remove water at the toluene azeotrope
  2. customthe mixture was evaporated in vacuo
  3. additionTo the residue in methanol (60 ml) was added sodium borohydride (1.2 g) under nitrogen at 5° C.
  4. additionThe resulting mixture was poured into ice-cold water
  5. stirringstirred for 30 minutes
  6. customAfter separation
  7. washthe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was chromatographed (hexane-ethyl acetate-methanol) over silica gel

출처 및 근거

ORD 기록
ord-0d1ccb447bc54a4aaee7dc639e12ceca
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495546B1

반응 노트

불러오는 중…