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

HRID 50995노트

반응식

HRID 50995 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 180011961-(3-Chloropropyl)indoline수율 45.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d9f402d892e4b6386e0c22bb95539d3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713471B1

반응 노트

불러오는 중…