Hydrochloric Acid → N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 1388056Notes

Reaction equation

C([N:3]1[C:9]2[CH:10]=[CH:11][C:12](C3C=CC(C)=CC=3)=[CH:13][C:8]=2[CH:7]=[C:6]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH3:38])[CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:26][CH:25]=2)=[O:22])[CH2:5][CH2:4]1)=O.Cl.C(=O)([O-])O.[Na+].O>C(OCC)(=O)C>[CH3:38][N:31]([CH2:30][C:27]1[CH:26]=[CH:25][C:24]([NH:23][C:21]([C:6]2[CH2:5][CH2:4][NH:3][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[CH:7]=2)=[O:22])=[CH:29][CH:28]=1)[CH:32]1[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1

Participants

Conditions

Temperature: 100 °C

Procedure

To 1-formyl-7-(4-methylphenyl)-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (1177 mg) was added 1N hydrochloric acid (20 ml), and the mixture was stirred at 100° C. for 1 hour. The mixture was dilute with ethyl acetate(50 ml) and made weakly basic with saturated sodium hydrogen carbonate solution (45 ml). To the mixture were added ethyl acetate (250 ml) and water (100 ml), and separated. The organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (75 g, ethyl acetate/ethanol=9:1) to give 7-(4-methyl-phenyl)phenyl)-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 318) (804 mg, 72%) as amorphous.

Workup

customseparated
dry with materialThe organic layer was dried with anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified with silica gel column chromatography (75 g, ethyl acetate/ethanol=9:1)

Sources & evidence

ORD record: ord-30a8b3d810c7422c9938de778e865865
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268354B1

Reaction notes

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