Methyl iodide → HCID 57849642, compound

HRID 737117Notes

Reaction equation

HRID 737117 reaction equation
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4C=[CH:24][CH:23]=[CH:22][C:21]=4C(F)(F)F)=[CH:16][CH:15]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:30](N(CC)C(C)C)(C)C.IC.Cl[CH2:42][Cl:43]>C(#N)C>[CH3:30][N:12]1[CH2:11][CH2:10][N:9]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:42]=3[Cl:43])=[CH:18][CH:19]=2)[CH2:8][CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 57849459HCID 57849459, compound

Product 1

HCID 57849642HCID 57849642, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

This compound could be made the following manner: 100 mg of 3-phenyl-1-(2′-trifluoromethyl-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-biphenyl-4-ylmethyl)-piperazine.

Workup

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

Sources & evidence

ORD record
ord-8554b311924e44d383b55e535fc0c808
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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