N-bromobutanimide → 4-(4-Amino-3-bromo-phenyl)-1-methyl-piperidine-2,6-dione

HRID 447994ノート

反応式

HRID 447994 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10](=[O:16])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:24])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][C:10](=[O:16])[N:11]([CH3:15])[C:12](=[O:14])[CH2:13]2)=[CH:6][C:7]=1[Br:24]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 597711294-(4-Amino-phenyl)-1-methyl-piperidine-2,6-dione

生成物 1

HCID 597712194-(4-Amino-3-bromo-phenyl)-1-methyl-piperidine-2,6-dione収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 289 mg (1.32 mmol) of 4-(4-amino-phenyl)-1-methyl-piperidine-2,6-dione (as prepared in the previous step) in CH2Cl2 (15 mL) was treated portionwise with 224 mg (1.29 mmol) of solid NBS for 20 min. The mixture was diluted with CH2Cl2 (30 mL) and washed with saturated aqueous NaHCO3 (2×30 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue with 25-50% EtOAc-hexane afforded 265 mg (67%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C12H13N2O2Br, 297.0/299.0 (M+H), found 297.0/299.0.

後処理

  1. washwashed with saturated aqueous NaHCO3 (2×30 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-46741b01cef5473caadce3b26c623545
出典データセット
uspto-grants-2013_07
特許番号
US08481564B2

反応ノート

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