Bromobenzene → (1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-[4-(3-thienyl)phenyl]propylamine

HRID 52855Notes

Reaction equation

HRID 52855 reaction equation
[C:1]1(Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:29]C2C=CC(Cl)=CC=2)[CH:16]([N:18]2C(=O)C3=CC=CC=C3C2=O)[CH3:17])=[CH:11][CH:10]=1.C([Sn](CCCC)(CCCC)[C:42]1[CH:46]=[CH:45][S:44][CH:43]=1)CCC.[Cl:55]C1C=CC(C2C=CC(C(CC3C=CC(Cl)=CC=3)C(N)C)=CC=2)=CC=1.ClC1C=CC(CC(C2C=CC(C3C=NC=CC=3)=CC=2)C(N)C)=CC=1.ClC1C=C(C2C=CC(C(CC3C=CC(Cl)=CC=3)C(N)C)=CC=2)C=CC=1.C1(C2C=CC=CC=2)C=CC=C(C(CC2C=CC(Cl)=CC=2)C(N)C)C=1.ClC1C=CC(CC(C2C=CC(C3C=CC4C(=CC=CC=4)C=3)=CC=2)C(N)C)=CC=1.ClC1C=CC(CC(C2C=CC(C3OC=CC=3)=CC=2)C(N)C)=CC=1.ClC1C=CC(CC(C2C=CC(C3C=CC4OCOC=4C=3)=CC=2)C(N)C)=CC=1.C1(C2C=CC=CC=2)C=CC=C(CC(C2C=CC(Cl)=CC=2)C(N)C)C=1.ClC1C=CC(C2C=CC(CC(C3C=CC(Cl)=CC=3)C(N)C)=CC=2)=CC=1.ClC1C=CC(C(CC2C=C(C3C=CC=CC=3)C(F)=CC=2)C(N)C)=CC=1.ClC1C=CC(C(CC2C=CC=C(C3C=CC4C(=CC=CC=4)C=3)C=2)C(N)C)=CC=1>>[Cl:55][C:1]1[CH:6]=[CH:5][C:4]([CH2:29][CH:15]([C:12]2[CH:11]=[CH:10][C:9]([C:42]3[CH:46]=[CH:45][S:44][CH:43]=3)=[CH:14][CH:13]=2)[CH:16]([NH2:18])[CH3:17])=[CH:3][CH:2]=1

Participants

15

Reactant 14

HCID 7961BromobenzeneHCID 10959689Stannane, tributyl-3-thienyl-HCID 19073589N-{(1RS,2RS)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropyl}phthalimideHCID 19073605(1RS, 2RS)-3-(3-biphenylyl)-2-(4-chlorophenyl)-1-methylpropylamineHCID 19073611(1RS, 2RS)-3-(4'-chloro-4-biphenylyl)-2-(4-chlorophenyl)-1-methylpropylamineHCID 19073612(1RS, 2RS)-2-(4-chlorophenyl)-1-methyl-3-[3-(2naphthyl)phenyl]propylamineHCID 19073635(1RS, 2RS)-3-(4-chlorophenyl)-2-{4-(2-furyl)phenyl}-1-methylpropylamineHCID 19073638(1RS, 2RS)-2-(3-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamineHCID 19073678(1RS, 2RS)-2-(4'-chloro-4-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamineHCID 19073680(1RS, 2RS)-2-(3'-chloro-4-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamineHCID 19073683(1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(2naphthyl)phenyl}propylamineHCID 19073763(1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-(3', 4'-methylenedioxy-4-biphenylyl)propylamineHCID 19073765(1RS, 2RS)-2-(4-chlorophenyl)-3-(6-fluoro-3-biphenylyl)-1-methylpropylamineHCID 19073786(1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-pyridyl)phenyl}propylamine

Product 1

HCID 19073735(1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-[4-(3-thienyl)phenyl]propylamine

Procedure

The following compounds were prepared in the same manner as in Example 117 using the corresponding phenyl bromide derivatives and/or aromatic stannane derivatives instead of N-{(1RS, 2RS)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropyl}phthalimide and/or tributyl(3-thienyl)tin used in the above reaction: (1RS, 2RS)-2-(4'-chloro-4-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-pyridyl)phenyl}propylamine, (1RS, 2RS)-2-(3'-chloro-4-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-2-(3-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(2naphthyl)phenyl}propylamine, (1RS, 2RS)-3-(4-chlorophenyl)-2-{4-(2-furyl)phenyl}-1-methylpropylamine, (1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-(3', 4'-methylenedioxy-4-biphenylyl)propylamine, (1RS, 2RS)-3-(3-biphenylyl)-2-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-3-(4'-chloro-4-biphenylyl)-2-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-2-(4-chlorophenyl)-3-(6-fluoro-3-biphenylyl)-1-methylpropylamine and (1RS, 2RS)-2-(4-chlorophenyl)-1-methyl-3-[3-(2naphthyl)phenyl]propylamine.

Workup

  1. customused in the above reaction

Sources & evidence

ORD record
ord-344dfb2779f4433189a15f9c04f0afcb
Source dataset
uspto-grants-1997_04
Patent number
US05616803

Reaction notes

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