1-Isopropylpiperazine → 1-[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]-4-isopropylpiperazine

HRID 922392노트

반응식

HRID 922392 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[N:3]=1.[CH:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:15])[CH3:14]>C(OCC)(=O)C>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[N:3]=[C:2]([N:19]2[CH2:20][CH2:21][N:16]([CH:13]([CH3:15])[CH3:14])[CH2:17][CH2:18]2)[CH:7]=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 780131-IsopropylpiperazineHCID 1186132-Bromo-6-(1,3-dioxolan-2-yl)pyridine

생성물 1

HCID 867193571-[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]-4-isopropylpiperazine수율 55%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

A mixture of 2-bromo-6-(1,3-dioxolan-2-yl)pyridine (7, 0.23 g, 1.0 mmol) and 1-isopropylpiperazine (0.38 g, 3.0 mmol) in a sealed tube was heated at 120° C. for 18 h. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water (10 mL), brine (10 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 0-10% methanol in dichloromethane to afford the title compound (0.15 g, 55%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 7.51-7.48 (m, 1H), 6.83-6.82 (m, 1H), 6.62-6.60 (m, 1H), 5.72 (s, 1H), 4.18-4.14 (m, 2H), 4.08-4.04 (m, 2H), 3.58 (br s, 4H), 2.71 (br s, 1H), 2.62 (br s, 2H), 1.08 (d, J=5.5 Hz, 6H); ESI MS m/z 278 [M+H]+.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water (10 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0-10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-9c9cbe803b03453dab40db7e6f392dc9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278940B2

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