Dimethyl Sulfoxide → [1-(4-Acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester

HRID 76080

반응식

HRID 76080 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:22])[CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:12].CS(C)=O>CCOCC>[CH2:11]([O:13][C:14](=[O:22])[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH2:18][CH2:17]1)[CH3:12]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 98284'-FluoroacetophenoneHCID 2760465Ethyl 2-(piperidin-4-yl)acetate

생성물 1

HCID 57442326[1-(4-Acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
150 °C

실험 절차

A microwave vial was charged with 4′-fluoroacetophenone (1.2 Ml, 10.4 mmol, 1.0 equiv) and 2-(piperidin-4-yl)-acetic acid ethyl ester (3.5 g, 20.7 mmol, 2.0 equiv) in 20 Ml DMSO. The homogeneous reaction was heated to 150° C. for 20 min. The cooled reaction was then diluted with ether and washed sequentially with saturated ammonium chloride, water, and brine. The organic extracts were then dried over sodium sulphate, filtered, and concentrated in vacuo. Purification by flash chromatography (10-40% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (t, J=7.07 Hz, 3H) 1.47 (d, J=12.13 Hz, 2H) 1.62 (br.s., 1H) 1.90 (d, J=12.63 Hz, 2H) 2.04-2.15 (m, J=11.18, 11.18, 7.45, 7.45, 3.79, 3.66 Hz, 1H) 2.33 (d, J=7.07 Hz, 2H) 2.57 (s, 3H) 2.97 (td, J=12.57, 2.15 Hz, 2H) 3.93 (d, J=12.88 Hz, 2H) 4.20 (q, J=7.07 Hz, 2H) 6.96 (d, J=6.82 Hz, 2H) 7.92 (d, J=9.09 Hz, 2H); (M+H)+290.1.

후처리

  1. customThe homogeneous reaction
  2. customThe cooled reaction
  3. washwashed sequentially with saturated ammonium chloride, water, and brine
  4. dry with materialThe organic extracts were then dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (10-40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-96dbcddc02ee40bf91e3618a3e3668a8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835451B2

연결된 노트

불러오는 중…