Benzaldehyde → N-{4-[trans-2-(benzylamino)cyclopropyl]phenyl}biphenyl-3-carboxamide

HRID 922526Notes

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]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)=[O:14])=[CH:8][CH:7]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+].[BH4-].[Na+]>CO.O>[CH2:27]([NH:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)=[O:14])=[CH:10][CH:11]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-[4-(trans-2-aminocyclopropyl)phenyl]biphenyl-3-carboxamide hydrochloride (130 mg) in methanol (4 mL) were added benzaldehyde (40 μL) and sodium hydrogen carbonate (49.9 mg). The mixture was stirred at 70° C. for 1 hr, and ice-cooled to 0° C. and sodium borohydride (22.5 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 recrystallized (hexane/ethyl acetate) to give the title compound (60.4 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 recrystallized (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-86e5d0fa6d69417289ddbbe92e408b7d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278931B2

Reaction notes

Loading…