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4-Methylmorpholine → 1-[3-(4-Cyano-phenyl)propionyl]-6-trifluoroacetylamino-1,2,3,4-tetrahydro-quinoline

HRID 379674
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인쇄 미리보기

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HRID 379674 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].CN1CCOCC1.ClC(OCC(C)C)=O.[F:29][C:30]([F:45])([F:44])[C:31]([NH:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[NH:40][CH2:39][CH2:38][CH2:37]2)=[O:32]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([N:40]2[C:41]3[C:36](=[CH:35][C:34]([NH:33][C:31](=[O:32])[C:30]([F:44])([F:45])[F:29])=[CH:43][CH:42]=3)[CH2:37][CH2:38][CH2:39]2)=[O:13])=[CH:7][CH:8]=1)#[N:2]
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7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 93617423-(4-Cyanophenyl)-propionic acidHCID 10421907N-(1,2,3,4-tetrahydro-6-quinolyl)trifluoroacetamide

생성물 1

HCID 154107711-[3-(4-Cyano-phenyl)propionyl]-6-trifluoroacetylamino-1,2,3,4-tetrahydro-quinoline

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 8857Ethyl Acetate용매

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온도
-20 °C

실험 절차

10 g (0.057 mol) of 3-(4-cyano-phenyl)propionic acid and 6.6 g (0.065 mol) of N-methyl-morpholine are dissolved in 250 ml tetrahydrofuran and cooled to −20° C. Then 8.2 g (0.06 mol) of isobutyl chloroformate are added dropwise. 13.9 g (0.057 mol) of 6-(trifluoroacetylamino)-1,2,3,4-tetrahydro-quinoline in 200 ml tetrahydrofuran are then added and the solution is left to heat up to ambient temperature overnight. It is then diluted with 200 ml of ethyl acetate and washed with 2×80 ml of 0.5 N hydrochloric acid and then 100 ml of sodium hydrogen carbonate solution. The organic phase is dried over sodium sulphate and concentrated by evaporation in vacuo.

후처리

  1. waitthe solution is left
  2. temperatureto heat up to ambient temperature overnight
  3. washwashed with 2×80 ml of 0.5 N hydrochloric acid
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo

출처 및 근거

ORD 기록
ord-bd685e2218f54e7ebfdb5b8910993818
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06300342B1

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