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

HRID 991498

반응식

HRID 991498 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ef4bc42f83794e03be0bdf36dd93c47d
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465485B1

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