Ammonium Chloride → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetylindoline

HRID 1790445노트

반응식

HRID 1790445 반응식
C([Li])CCC.[F:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25](Br)[CH:26]=4)[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[CH3:31][C:32](N(C)C)=[O:33].[Cl-].[NH4+]>CCCCCC.O1CCCC1.C(OCC)(=O)C>[F:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:32](=[O:33])[CH3:31])[CH:26]=4)[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 220378891-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindolineHCID 178418339Butyllithium

생성물 1

HCID 220381171-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetylindoline수율 27%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

A 2.5 M solution (1.5 ml) of n-butyllithium in hexane was added dropwise at −78° C. into a solution (30 ml) of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoindoline (1.0 g) in tetrahydrofuran over 5 min. After 10 min, dimethylacetamide (0.34 ml) was added thereto and the resultant mixture was warmed to room temperature. Next, a saturated aqueous solution of ammonium chloride and ethyl acetate were added thereto to and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (250 mg) as a yellow powder (yield: 27%).

후처리

  1. customto and the 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 residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system)

출처 및 근거

ORD 기록
ord-e3eec821340f44e9a277867fc7a6326b
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071201B2

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