1-Bromo-3-chloropropane → 1-(3-Chloropropyl)indoline

HRID 1764871ノート

反応式

HRID 1764871 の反応式
Br[CH2:2][CH2:3][CH2:4][Cl:5].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1.CCN(CC)CC>O1CCOCC1>[Cl:5][CH2:4][CH2:3][CH2:2][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 10328Indoline

生成物 1

HCID 180011961-(3-Chloropropyl)indoline収率 45.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

To a solution of 1-bromo-3-chloropropane (1.98 g, 12.6 mmol) and indoline (500 mg, 4.20 mmol) in 1,4-dioxane (6.0 mL) was added Et3N (2.12 g, 21.0 mmol) at 20° C. The reaction mixture was then stirred for 15 h at 70° C. The reaction mixture was cooled to 20° C. and quenched by addition of H2O. The product was extracted with Et2O. The organic solution was then washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. 1-(3-Chloro-1-propyl)indoline (373 mg, 45%) was isolated by flash chromatography on a silica gel column by elution with EtOAc/Hexanes a pale yellow oil. 1H NMR (CDCl3, 300 MHz) δ2.07 (qu, 2H, J=6.2 Hz), 2.97 (t, 2H, J=8.2 Hz), 3.24 (t, 2H, J=6.6 Hz), 3.35 (t, 2H, J=8.3 Hz), 3.68 (t, 2H, J=6.2 Hz), 6.50-6.56 (m, 1H), 6.66 (t, 1H, J=6.6 Hz), 7.04-7.10 (m, 2H) ppm.

後処理

  1. temperatureThe reaction mixture was cooled to 20° C.
  2. customquenched by addition of H2O
  3. extractionThe product was extracted with Et2O
  4. washThe organic solution was then washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ce9610e188ae45d48093dfe362596894
出典データセット
uspto-grants-2007_06
特許番号
USRE039679E1

反応ノート

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