Potassium Carbonate → 1,2,3,4-Tetrahydro-7-methoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline

HRID 1451657

반응식

HRID 1451657 반응식
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][NH:21][CH2:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH3:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][N:21]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=3)[CH2:22]2)=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 4172887-Methoxy-1,2,3,4-Tetrahydroisoquinoline

생성물 1

HCID 199745591,2,3,4-Tetrahydro-7-methoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline수율 31.8%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 1-(2-bromoethyl)-4-nitrobenzene (3.7 g), 1,2,3,4-tetrahydro-7-methoxyisoquinoline (2.7 g; Daniel J. Sall and Gary L. Grunewald, J. Med. Chem. 1987, 30, 2208-2216) and potassium carbonate (6.7 g) in isopropanol (150 ml) was stirred under reflux for 48 h. The mixture was evaporated to dryness, and the residue was extracted with dichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was then purified by column chromatography elating with dichloromethane/methanol (99:1) to give the title compound (1.6 g) as an orange solid, MP: 92°-94°. NMR includes signals at d 3.6 (2H,m,N--CH2Ar), 3.7 (3H,s,OCH3).

후처리

  1. temperatureunder reflux for 48 h
  2. customThe mixture was evaporated to dryness
  3. extractionthe residue was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was then purified by column chromatography

출처 및 근거

ORD 기록
ord-54cde512ca574c9ea3ec4cc684c3ba64
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604237

연결된 노트

불러오는 중…