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

HRID 2299653ノート

反応式

HRID 2299653 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0d1ccb447bc54a4aaee7dc639e12ceca
出典データセット
uspto-grants-2002_12
特許番号
US06495546B1

反応ノート

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