1,2,3,4-Tetrahydroisoquinoline → 1,2,3,4-Tetrahydro-2-[3-(4-nitrophenoxy)propyl]isoquinoline

HRID 1451656노트

반응식

HRID 1451656 반응식
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[CH2:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][NH:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:16]2[CH2:17][CH2:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15]2)=[CH:7][CH:8]=1)([O-:14])=[O:13]

참가 물질

5

반응물 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 2611281-(3-Bromopropoxy)-4-nitrobenzene

생성물 1

HCID 103808031,2,3,4-Tetrahydro-2-[3-(4-nitrophenoxy)propyl]isoquinoline수율 73.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1-(3-bromopropoxy)-4-nitrobenzene (10 g), 1,2,3,4-tetrahydroisoquinoline (5.1 g) and potassium carbonate (10.6 g) in DMF (100 ml) was stirred at 70° for 24 h. The mixture was then filtered and the filtrate evaporated. The residue was taken up with water and extracted with dichloromethane. The organic layer was washed with water, dried, evaporated and purified by column chromatography eluting with dichloromethane/methanol (96:4) to give the title compound (8.8 g) as a yellow oil. NMR includes signals at d 3.6 (2H,s,N--CH2Ar), 4.1 (2H,t,O--CH2).

후처리

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography
  8. washeluting with dichloromethane/methanol (96:4)

출처 및 근거

ORD 기록
ord-34d0f8ace30a4d25bf0afd0adcc6e962
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604237

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