Hydrochloric Acid → HCID 20540750, compound

HRID 1065509Notes

Reaction equation

Br[CH2:2][C:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]=1[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(O)C.O.C(O)C>[ClH:18].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([OH:31])[CH2:26][CH2:27][N:28]([CH2:2][C:3]3[NH:7][C:6](=[O:8])[NH:5][C:4]=3[C:9](=[O:17])[C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[CH2:29][CH2:30]2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4.3 g (14.2 mmole) of 5-(bromomethyl)-1,3-dihydro-4-(4-fluorobenzoyl)-2H-imidazol-2-one, 3.0 g (14.2 mmole) of 4-(4-chlorophenyl)-4-hydroxypiperidine, 2.0 g (14.2 mmole) of potassium carbonate and 75 ml of ethanol is stirred under argon for 16 hours at 25° C. Water (100 ml) is added and the precipitate which forms is collected 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 and recrystallized twice from a mixture of 2-propanol and water to give 4-[[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]methyl]-5-(4-fluorobenzoyl)-1,3-dihydro-2H-imidazol-2-one hydrochloride melting at about 235°-236° C. with decomposition.

Workup

customthe precipitate which forms is collected
washwashed with water
customThe resulting solid is separated
customrecrystallized twice from a mixture of 2-propanol and water

Sources & evidence

ORD record: ord-b7f46120441646dda1acaa08d583b8f1
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04329471

Reaction notes

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