Hydrochloric Acid → 1,3-dihydro-4-(4-methoxybenzoyl)-5-[(4-phenyl-1-piperidinyl)methyl]-2H-imidazol-2-one hydrochloride

HRID 1065508Notes

Reaction equation

Br[CH2:2][C:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.[C:19]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:37]>CC(O)C.O.C(O)C>[ClH:37].[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([C:4]2[NH:5][C:6](=[O:8])[NH:7][C:3]=2[CH2:2][N:28]2[CH2:29][CH2:30][CH:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)=[O:18])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4.7 g (15 mmole) of 5-(bromomethyl)-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one, 2.5 g (16 mmole) of 4-phenylpiperidine, 2.1 g (15 mmole) of potassium carbonate and 75 ml of ethanol is stirred at 25° C. for 16 hours. Water (100 ml) is added and a precipitate forms. This is separated by filtration and washed with water. It is then suspended in 2-propanol and 1 equivalent of hydrogen chloride in 2-propanol is added. The resulting solid is separated by filtration and recrystallized from 2-propanol containing a little water to give 1,3-dihydro-4-(4-methoxybenzoyl)-5-[(4-phenyl-1-piperidinyl)methyl]-2H-imidazol-2-one hydrochloride melting at about 230° C. with decomposition.

Workup

customThis is separated by filtration
washwashed with water
customThe resulting solid is separated by filtration
customrecrystallized from 2-propanol containing a little water

Sources & evidence

ORD record: ord-a5db4d3cd93d4b4d86ff421989ec18b1
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04329471

Reaction notes

Loading…