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

HRID 930163Notes

Reaction equation

HRID 930163 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-7ca88d0f31dd4d92a546fd0de7455eaa
Source dataset
uspto-grants-2016_03
Patent number
US09296726B2

Reaction notes

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