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

HRID 1452414Notes

Reaction equation

HRID 1452414 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 cross-coupling product thus obtained was suspended in 4 ml of ethanol, and 0.1 ml of hydrazine monohydrate was added thereto. The mixture was heated under reflux for 5 hours. The reaction solution was evaporated to dryness under reduced pressure. Then, the residue was dissolved in 10 ml of methylene chloride. Insoluble matters were separated by filtration, and then the solvent was evaporated to dryness under reduced pressure to obtain 56 mg (yield: 68%) of the above-identified compound as colorless oily substance. 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-(2-naphthyl)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-(2-naphthyl)phenyl]propylamine.

Workup

  1. customused in the above reaction

Sources & evidence

ORD record
ord-e39ca09360b44bbc833476c0b2360bd5
Source dataset
uspto-grants-1997_02
Patent number
US05606101

Reaction notes

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