Benzoyl chloride → N-[2-(3,4-Dichlorophenyl)-2-(4-hydroxy-4-phenylpiperidino)ethyl]-N-methylbenzamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:13]2[CH2:18][CH2:17][C:16]([OH:25])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH2:10][NH:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.C(OCC)C.CCCCCC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:13]2[CH2:14][CH2:15][C:16]([OH:25])([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:17][CH2:18]2)[CH2:10][N:11]([CH3:12])[C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
6
Procedure
N-[2-(3,4-Dichlorophenyl)-2-(4-hydroxy-4-phenylpiperdino)-ethyl]methylamine (450 mg), benzoyl chloride (168 mg), and triethylamine (120 mg) in tetrahydrofuran were stirred at 23° C. for 48 hours. The reaction was filtered concentrated to a gold oil. Chromatography, with chloroform and then methanol:chloroform (5:95) as the eluent, gave a gold oil. Trituration of the oil with diethylether/hexane provided a white solid; MS: m/z=483(M+1); NMR: 1.77 (m,2), 2.4 (m,1), 2.63 (m,1), 2.72 (m,3), 3.2 (m,3), 3.83 (m,1), 4.36 (m,2), 4.93 (m,1), 5.43 (broad s,1), 7.03 (m,2), 7.41 (m,7), 7.83 (m,2). Analysis Calculated: C, 60.28; H, 5.8; N, 5.21; Found: C, 60.25; H, 5.52; N, 5.14.
Workup
- filtrationThe reaction was filtered
- concentrationconcentrated to a gold oil
- customChromatography, with chloroform and then methanol:chloroform (5:95) as the eluent, gave a gold oil
Sources & evidence
- ORD record
- ord-f08518aa123b4be6a52eb7224c0bc9e6
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998444
Reaction notes
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