Sodium Iodide → HCID 69222715, compound

HRID 971218Notes

Reaction equation

HRID 971218 reaction equation
[I-].[Na+].I.[CH2:4]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([NH2:22])=[CH:16][C:17]=2Cl)[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1>O1CCOCC1>[CH2:4]([N:11]1[CH2:20][CH2:19][C:18]2[C:17]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=3)=[CH:16][C:15]([NH2:22])=[CH:14][C:13]=2[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 99644-(Trifluoromethyl)anilineHCID 24841Hydrogen iodideHCID 69221623HCID 69221623, compound

Product 1

HCID 69222715HCID 69222715, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Sodium iodide (252 mg, 1.68 mmol) and hydriodic acid (1 mL, 47% aqueous solution) were added to the solution of 2-benzyl-5-chloro-1,2,3,4-tetrahydroisoquinolin-7-amine (380 mg, 1.4 mmol) and 4-aminobenzotrifluoride (446 mg, 2.8 mmol) in dioxane (10 mL) and the reaction solution was stirred at 100° C. over night before solvent was removed in vacuo. Residue was dissolved in ethyl acetate, washed by water, brine, dried over sodium sulfate and was purified by column chromatography. Product was obtained as brown oil (440 mg, 79%).

Workup

  1. customwas removed in vacuo
  2. dissolutionResidue was dissolved in ethyl acetate
  3. washwashed by water, brine
  4. dry with materialdried over sodium sulfate
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-69f58fe0677c4a0c8d4a4dd471caba0b
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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