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2-(Dimethylamino)ethanol → 2-(Dimethylamino)ethyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate

HRID 256691
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HRID 256691 반응식
[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([OH:17])=[O:16])[CH:4]=[C:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O1CCOCC1.CN(C)C1C=CN=CC=1>[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([O:17][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])=[O:16])[CH:4]=[C:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 79022-(Dimethylamino)ethanolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate2회HCID 156408234,6-Dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylic acid

생성물 1

HCID 189570492-(Dimethylamino)ethyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 312751,4-Dioxane용매

실험 절차

A suspension of 9.0 g of 4,6-dihydro-4-oxo-3-phenyl-pyrido[2,1-a]isoindole-1-carboxylic acid in 240 ml of dioxane was treated in succession with 6.7 ml of 2-(dimethylamino)ethanol, 15.7 g of 1H-1-benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate and 263 mg of 4-dimethylaminopyridine, whereupon the mixture was heated to boiling under reflux for 80 minutes under argon, treated with 1.58 g of 1-benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate and heated for a further 1 hour. The mixture was then left to cool and the separated crystals were filtered off under suction. After stirring with 890 ml of methylene chloride, 475 ml of water and 70 ml of saturated sodium hydrogen carbonate solution for 90 minutes the organic phase was separated and evaporated. The residue was dissolved in 100 ml of methanol, whereupon the solution was acidified with ethereal hydrochloric acid, filtered and the product was precipitated by cooling in an ice bath. There was obtained 2.9 g of 2-(dimethylamino)ethyl 4,6dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate as yellowish crystals with a m.p. of 225°-228°.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 80 minutes under argon
  3. temperatureheated for a further 1 hour
  4. waitThe mixture was then left
  5. temperatureto cool
  6. filtrationthe separated crystals were filtered off under suction
  7. customwas separated
  8. customevaporated
  9. dissolutionThe residue was dissolved in 100 ml of methanol, whereupon the solution
  10. filtrationfiltered
  11. customthe product was precipitated
  12. temperatureby cooling in an ice bath

출처 및 근거

ORD 기록
ord-f4038d07a4314a4d921e856f8b1166f5
출처 데이터셋
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05258387

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