Sodium hydride → 1-(4-Bromo-2,6-dichloro-benzyl)-3-piperidin-1-yl-pyrrolidin-2-one

HRID 1670841노트

반응식

HRID 1670841 반응식
[N:1]1([CH:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Br:15][C:16]1[CH:17]=[C:18]([Cl:25])[C:19]([CH2:23]Br)=[C:20]([Cl:22])[CH:21]=1>CN(C=O)C.C(OCC)C>[Br:15][C:16]1[CH:17]=[C:18]([Cl:25])[C:19]([CH2:23][N:9]2[CH2:10][CH2:11][CH:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:8]2=[O:12])=[C:20]([Cl:22])[CH:21]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 576580133-Piperidin-1-yl-pyrrolidin-2-oneHCID 594744985-Bromo-2-(bromomethyl)-1,3-dichlorobenzene

생성물 1

HCID 576580161-(4-Bromo-2,6-dichloro-benzyl)-3-piperidin-1-yl-pyrrolidin-2-one수율 90.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

Treat a solution of 3-piperidin-1-yl-pyrrolidin-2-one (0.33 g, 1.96 mmol) in DMF (6 mL) with 60% sodium hydride (0.12 g, 3.00 mmol) and stir at room temperature for 15 minutes under N2. Cool the reaction to 0° C., treat with 5-bromo-2-(bromomethyl)-1,3-dichlorobenzene (0.70 g, 2.19 mmol), stir for 15 minutes at 0° C., warm to room temperature, and stir for 3 hours under N2. Quench the reaction with water and dilute with diethyl ether. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 0 to 5% methanol in CH2Cl2 gradient to afford 0.718 g (90%) of the titled product. Rf=0.29 (9/1 CH2Cl2/methanol). ES MS (m/z): 407 (M+).

후처리

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. stirringstir for 15 minutes at 0° C.
  4. temperaturewarm to room temperature
  5. stirringstir for 3 hours under N2
  6. customQuench
  7. customthe reaction with water
  8. dry with materialDry the organic layer (Na2SO4)
  9. customremove the solvent in vacuo
  10. customto afford crude product
  11. custompurify with a 0 to 5% methanol in CH2Cl2 gradient

출처 및 근거

ORD 기록
ord-aeb6cb6781fb4c83b33dc3f71cb4614b
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994176B2

반응 노트

불러오는 중…