Methyl iodide → (1S,2S)-N-benzyl-2-(4-biphenylyl)-3-(3,4-dichlorophenyl)-1-methylpropylamine

HRID 52858Notes

Reaction equation

HRID 52858 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([C@H:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[C@@H:8]([NH2:10])[CH3:9])=[CH:3][CH:2]=1.CI.[Cl:28][C:29]1[CH:30]=[C:31]([CH2:36][C@@H:37]([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[C:43]([F:53])[CH:42]=2)[C@@H:38]([NH2:40])[CH3:39])[CH:32]=[CH:33][C:34]=1[Cl:35].[CH2:54](Cl)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>>[Cl:28][C:29]1[CH:30]=[C:31]([CH2:36][C@@H:37]([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[C:43]([F:53])[CH:42]=2)[C@@H:38]([NH:40][CH3:1])[CH3:39])[CH:32]=[CH:33][C:34]=1[Cl:35].[CH2:54]([NH:10][C@@H:8]([CH3:9])[C@H:7]([C:4]1[CH:3]=[CH:2][C:1]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:6][CH:5]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7503Benzyl ChlorideHCID 10905181(1S,2S)-3-(3,4-dichlorophenyl)-2-(2-fluoro-4-biphenylyl)-1-methylpropylamineHCID 56979232HCID 56979232, compound

Product 2

HCID 57016219(1S,2S)-N-benzyl-2-(4-biphenylyl)-3-(3,4-dichlorophenyl)-1-methylpropylamineHCID 57256647(1S,2S)-N-{3-(3,4-dichlorophenyl)-2-(2-fluoro-4-biphenylyl)-1-methylpropyl}methylamine

Procedure

The reaction was conducted in the same manner as in Example 121 except that (1S, 2S)-2-(4-biphenylyl)-3-(3,4-dichlorophenyl)-1-methylpropylamine or methyl iodide used in the above reaction was changed to (1S, 2S)-3-(3,4-dichlorophenyl)-2-(2-fluoro-4-biphenylyl)-1-methylpropylamine or benzyl chloride, to obtain (1S, 2S)-N-{3-(3,4-dichlorophenyl)-2-(2-fluoro-4-biphenylyl)-1-methylpropyl}methylamine and (1S, 2S)-N-benzyl-2-(4-biphenylyl)-3-(3,4-dichlorophenyl)-1-methylpropylamine.

Workup

  1. customused in the above reaction

Sources & evidence

ORD record
ord-c1891e57c645430ca618a7683cd1c86a
Source dataset
uspto-grants-1997_04
Patent number
US05616803

Reaction notes

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