N-Benzoyl-4-piperidone → HCID 178479671, compound

HRID 1355579Notes

Reaction equation

[ClH:1].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C@H:12]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)[NH2:13])=[CH:3]1.[C:25]([N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)(C)C>[ClH:1].[C:19]1([C:17]2[N:18]=[C:14]([C@H:12]3[CH2:11][C:4]4[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[NH:2][C:3]=4[C:36]4([CH2:37][CH2:38][N:33]([C:25](=[O:32])[C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH2:34][CH2:35]4)[NH:13]3)[NH:15][CH:16]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of (1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine hydrochloride (1 g, 2.65 mmol) in isopropanol (15 ml) was added N-benzoyl-4-piperidone (2.64 g, 13 mmol). The solution was refluxed for about one hour and cooled to about 20° C. The solvent was removed under reduced pressure. The residue was treated with dichloromethane (30 ml) and stirred for about 30 min at about 20° C. The resulting precipitate was collected by filtration, washed with dichloromethane and diethyl ether, and dried to afford 1.2 g of the title product as the hydrochloride salt. Melting point: 240-244° C.

Workup

temperatureThe solution was refluxed for about one hour
customThe solvent was removed under reduced pressure
additionThe residue was treated with dichloromethane (30 ml)
filtrationThe resulting precipitate was collected by filtration
washwashed with dichloromethane and diethyl ether
customdried

Sources & evidence

ORD record: ord-3e0ff5be7cd149cfbd204c6d7dd67b14
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586445B1

Reaction notes

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