3-Iodo-4-methylbenzoyl chloride → 3-iodo-4-methyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide

HRID 1042633Notes

Reaction equation

HRID 1042633 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH2:19])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)[CH2:4][CH2:3]1.[I:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:24](Cl)=[O:25]>C(Cl)Cl>[I:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:24]([NH:19][C:11]1[CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:14]=[C:9]([CH2:8][N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[CH:10]=1)=[O:25]

Participants

4

Reactant 2

HCID 177521573-Iodo-4-methylbenzoyl chlorideHCID 231550523-((4-Methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)aniline

Product 1

HCID 594279993-iodo-4-methyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)-benzenamine (0.274 g, 1 mmol) in CH2Cl2 (3 mL) at room temperature was added 3-iodo-4-methylbenzoyl chloride (0.267 g, 0.95 mmol). The mixture was allowed to stir for 20 h. The reaction was concentrated under reduced pressure, and purified via column chromatography (0 to 20% methanol in dichloromethane) to afford 3-iodo-4-methyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide. MS m/z=518. Calc'd for C24H18ClF3N4O: 517.33.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. custompurified via column chromatography (0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-198feb7f5eff4ba4ba35dec71cc28c4c
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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