Methyl iodide → 1-Methyl-2-phenyl-4-(2'-chloro-5'-methyl-biphenyl-4-ylmethyl)-piperazine

HRID 737137Notes

Reaction equation

[CH2:1]([CH:8]1[NH:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=3[Cl:28])=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.[CH:29](N(CC)C(C)C)(C)C.IC>C(#N)C.ClCCl>[CH3:29][N:13]1[CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=3[Cl:28])=[CH:17][CH:16]=2)[CH2:9][CH:8]1[C:1]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

This compound could be made the following manner: 100 mg of 3-benzyl-1-(2′-chloro-5′-methyl-biphenyl-4-ylmethyl)-piperazine would be dissolved in acetonitrile, 3 equiv. of N,N-diisopropylethylamine would be added followed by 1.1 equiv. of iodomethane. The reaction would be stirred at 80° C. overnight. The reaction would be diluted with dichloromethane and washed with 1N aqueous NaOH solution. The organic layer would be dried over Na2SO4, filtered and concentrated in vacuo. The crude residue would be purified by column chromatography to afford 1-methyl-2-phenyl-4-(2′-chloro-5′-methyl-biphenyl-4-ylmethyl)-piperazine.

Workup

customThe reaction
customThe reaction
washwashed with 1N aqueous NaOH solution
dry with materialThe organic layer would be dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue would be purified by column chromatography

Sources & evidence

ORD record: ord-c0c205d68ac345f886eea1d2f4e8253d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595397B2

Reaction notes

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