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

HRID 930126Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:23])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:15])[NH:11][C:12](=[O:14])[CH2:13]2)=[CH:6][C:7]=1[Br:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 106 mg (0.519 mmol) of 4-(4-amino-phenyl)-piperidine-2,6-dione (as prepared in the previous step) in CH2Cl2 (20 mL) was cooled to 0° C. and treated with 92.4 mg (0.519 mmol) of NBS for 35 min. The mixture was diluted with CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (2×40 mL) and water (1×40 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 138 mg (94%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C11H11N2O2Br, 283.0/285.0 (M+H). found 283.1/285.1.

Workup

washwashed with saturated aqueous NaHCO3 (2×40 mL) and water (1×40 mL)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-28b9b959120943ec8b87543835ca6254
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296726B2

Reaction notes

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