N-bromobutanimide → 1-[4-(4-Amino-3-bromo-phenyl)-piperidin-1-yl]-ethanone

HRID 1043317Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][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:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[Br:24]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-[4-(4-amino-phenyl)-piperidin-1-yl]-ethanone (as prepared in the previous step, 0.36 g, 1.66 mmol) in CH2Cl2 (10 mL) was cooled to −78° C. and treated with NBS (0.28 g, 1.58 mmol) as a suspension in CH2Cl2 (4 mL). The reaction was allowed to warm to room temperature and stir for 30 min. The reaction was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated in vacuo. The crude material was used directly in the next reaction. LC-MS (ESI, m/z): Calcd. for C13H17BrN2O 297.1 (M+H). found 297.1.

Workup

temperatureto warm to room temperature
washwashed with saturated aqueous NaHCO3
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customThe crude material was used directly in the next reaction

Sources & evidence

ORD record: ord-0c8240d9558d4292b2019f5743d14383
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557847B2

Reaction notes

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