1-Methyl-4-piperidone → 3-bromo-N-(4-{trans-2-[(1-methylpiperidin-4-yl)amino]cyclopropyl}phenyl)benzamide

HRID 922498Notes

Reaction equation

Cl.[NH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=2)=[CH:8][CH:7]=1.[CH3:22][N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.C(=O)([O-])O.[Na+].[BH4-].[Na+]>CO.O>[Br:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([C@@H:4]2[CH2:5][C@H:3]2[NH:2][CH:26]2[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]2)=[CH:7][CH:8]=1)=[O:21]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-[4-(trans-2-aminocyclopropyl)phenyl]-3-bromobenzamide hydrochloride (80 mg) in methanol (2 mL) were added 1-methylpiperidin-4-one (24.6 mg) and sodium hydrogen carbonate (27.4 mg). The mixture was stirred at 70° C. for 1 hr, and ice-cooled to 0° C. and sodium borohydride (12.4 mg) was added. The mixture was stirred for 1 hr and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized (ethyl acetate) to give the title compound (10.0 mg).

Workup

temperatureice-cooled to 0° C.
stirringThe mixture was stirred for 1 hr
extractionThe mixture was extracted with ethyl acetate
washthe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate)
customrecrystallized (ethyl acetate)

Sources & evidence

ORD record: ord-da43b7072cbf453fa3765252989a5694
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278931B2

Reaction notes

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