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

HRID 1451657

反応式

HRID 1451657 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-54cde512ca574c9ea3ec4cc684c3ba64
出典データセット
uspto-grants-1997_02
特許番号
US05604237

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