Iodide Ion → N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide

HRID 1527884Notes

Reaction equation

HRID 1527884 reaction equation
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)([CH3:4])=[O:3].[I:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[CH3:34])[C:28](Cl)=[O:29].C(N(C(C)C)CC)(C)C.[I-]>ClCCl>[CH3:4][P:2]([CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH2:12][C:13]2[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][C:16]([NH:17][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][C:33]([CH3:34])=[C:25]([I:24])[CH:26]=3)=[CH:15][CH:14]=2)[CH2:10][CH2:11]1)([CH3:1])=[O:3]

Participants

6

Reactant 4

HCID 30165Iodide IonHCID 81531DiisopropylethylamineHCID 177521573-Iodo-4-methylbenzoyl chlorideHCID 689121604-({4-[(Dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)aniline

Product 1

HCID 68911921N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-5-(trifluoromethyl)aniline (yellow solid, 3.66 mmole, 1.0 eq.) was dissolved in 15 mL anhydrous dichloromethane. 3-iodo-4-methylbenzoyl chloride (1.58 grams, 5.64 mmole, 1.54 eq.) was added in one portion. At 0° C., under N2 protection, diisopropylethyl amine (2.4 mL, 14.0 mmole, 3.8 eq.) was added dropwise in 3 minutes. The reaction mixture was stirred at 0° C. under N2 for 30 minutes. It was then evaporated to remove most of the volatile components. The residue was purified via column chromatography (elution sequence: 100% dichloromethane-1% MeOH/dichloromethane/sat.NH3-10% MeOH/dichloromethane/sat.NH3). 40 mg of light yellow color oil was obtained and identified as the desire iodide. MS (LC/MS): 592.3 [M−].

Workup

  1. customIt was then evaporated
  2. customto remove most of the volatile components
  3. customThe residue was purified via column chromatography (elution sequence: 100% dichloromethane-1% MeOH/dichloromethane/sat.NH3-10% MeOH/dichloromethane/sat.NH3)
  4. custom40 mg of light yellow color oil was obtained

Sources & evidence

ORD record
ord-b4df66fd372546b1b82794e1cb7e477b
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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