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

HRID 1670841ノート

反応式

HRID 1670841 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-aeb6cb6781fb4c83b33dc3f71cb4614b
出典データセット
uspto-grants-2011_08
特許番号
US07994176B2

反応ノート

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