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

HRID 1790505ノート

反応式

HRID 1790505 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-286c2e757c554ba2b8f51cc0a8f53262
出典データセット
uspto-grants-2006_07
特許番号
US07071201B2

反応ノート

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