Sodium Carbonate → 1-(5-Chloro-2-nitro-phenyl)-4-fluoro-piperidine

HRID 646946

반응식

HRID 646946 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].Cl.[F:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:23]2[CH2:24][CH2:25][CH:20]([F:19])[CH2:21][CH2:22]2)[CH:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 27591584-Fluoropiperidine hydrochloride

생성물 1

HCID 586385111-(5-Chloro-2-nitro-phenyl)-4-fluoro-piperidine수율 100.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
40 °C

실험 절차

A solution of 4-chloro-2-fluoro-1-nitro benzene (0.30 g, 1.7 mmol) in toluene (5 mL) was treated with solid Na2CO3 (0.40 g, 3.7 mmol) and 4-fluoropiperidine hydrochloride (0.25 g, 1.8 mmol). The reaction was heated to 40° C. for 6 h. The reaction was diluted with EtOAc and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound (0.44 g, 99%) as a bright yellow oil. 1H-NMR (CDCl3; 400 MHz): δ 7.79 (d, 1H, J=8.8 Hz), 7.10 (d, 1H, 2.0 Hz), 6.97 (dd, 1H, J=8.8 Hz, J=2.0 Hz), 4.97-4.79 (m, 1H), 3.26-3.17 (m, 2H), 3.06-2.99 (m, 2H), 2.14-1.97 (m, 4H). LC-MS (ESI, m/z): Calcd. for C11H12ClFN2O2, 225.2 (M-Cl+2H), found 225.2.

후처리

  1. washwashed with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a385bb61f5cc4dbe885cff2e44e4ab10
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705042B2

연결된 노트

불러오는 중…