Ammonia → 5-Pentafluoroethyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline

HRID 991498

反応式

HRID 991498 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:7]2.[F:18][C:19]([F:27])([F:26])[C:20]([F:25])([F:24])C([O-])=O.[Na+].C1(C)C=CC=CC=1.N>[Cu]I.O.CN(C)C=O>[F:24][C:20]([F:25])([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:7]2)[C:19]([F:27])([F:26])[F:18]

参加物

8

反応物 4

HCID 222AmmoniaHCID 1140TolueneHCID 2733305Sodium pentafluoropropionateHCID 184142741-(5-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

生成物 1

HCID 184142825-Pentafluoroethyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline収率 66%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (4.0 g, 13 mmol), sodium pentafluoropropionate (4.85 g, 26 mmol), copper (I) iodide (5.22 g, 27.2 mmol), toluene (70 ml) and dimethylformamide (70 ml) was heated under argon with Dean-Stark distillation (70 ml distillate collected), then heated at reflux for 18 h. The mixture was cooled, then poured into a mixture of water (150 ml) and 0.880 ammonia (150 ml). Resulting solution was extracted with dichloromethane (4×100 ml) and the combined extracts dried (Na2SO4) and evaporated in vacuo to give a solid. Chromatography on silica with 10-50% ether-hexane gradient elution gave the title compound (2.97 g, 66%) as a colourless solid.

後処理

  1. temperaturewas heated under argon with Dean-Stark distillation (70 ml distillate collected)
  2. temperatureheated
  3. temperatureat reflux for 18 h
  4. temperatureThe mixture was cooled
  5. extractionResulting solution was extracted with dichloromethane (4×100 ml)
  6. dry with materialthe combined extracts dried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give a solid
  9. washChromatography on silica with 10-50% ether-hexane gradient elution

出典と根拠

ORDレコード
ord-ef4bc42f83794e03be0bdf36dd93c47d
出典データセット
uspto-grants-2002_10
特許番号
US06465485B1

関連ノート

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