Dimethylformamide → 1-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-formylindoline

HRID 1790505노트

반응식

HRID 1790505 반응식
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18](Br)[CH:19]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1.CN(C)[CH:28]=[O:29].[Cl-].[NH4+].C(OCC)(=O)C>CCCCCC.O1CCCC1>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:28]=[O:29])[CH:19]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 220380011-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-bromoindoline

생성물 1

HCID 220379081-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-formylindoline수율 91.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A 1.6 M solution (24 ml) of n-(butyllithium) in hexane was added dropwise at −78° C. over 10 min into a solution of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-bromoindoline (12 g) obtained in Example 348-2) in tetrahydrofuran (200 ml). After 10 min, dimethylformamide (3.5 ml) was added thereto and the resultant mixture was allowed to warm to room temperature. Then a saturated aqueous solution (100 ml) of ammonium chloride and ethyl acetate (200 ml) were added thereto and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting obtained was purified by silica gel column chromatography (ethyl acetate/ethanol system) to give the title compound (9.6 g) as a yellow powder (yield: 91.5%).

후처리

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting obtained
  6. customwas purified by silica gel column chromatography (ethyl acetate/ethanol system)

출처 및 근거

ORD 기록
ord-286c2e757c554ba2b8f51cc0a8f53262
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071201B2

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