Potassium Iodide → Hydrochloric Acid

HRID 2303361Notes

Reaction equation

HRID 2303361 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:35][CH2:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:43]2[CH:48]=[C:47]([O:49][CH3:50])[C:46]([O:51][CH3:52])=[C:45]([O:53][CH3:54])[CH:44]=2)[CH:38]=1>C(#N)C>[O:1]=[C:2]1[CH2:7][N:6]([CH2:36][C:37]2[CH:42]=[CH:41][N:40]=[C:39]([C:43]3[CH:48]=[C:47]([O:49][CH3:50])[C:46]([O:51][CH3:52])=[C:45]([O:53][CH3:54])[CH:44]=3)[CH:38]=2)[CH2:5][CH2:4][N:3]1[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)[CH:10]=1.[ClH:35]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 120192374-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridineHCID 120192382-Oxo-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperazine

Product 2

HCID 313Hydrochloric AcidHCID 102824962-oxo-N,N'-bis[[2-(3,4,5-trimethoxyphenyl)-pyridin-4-yl]methyl]piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

2-Oxo-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperazine (62 mg) was dissolved in acetonitrile (5 mL), and to the solution potassium carbonate (24 mg), potassium iodide (29 mg) and 4-chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridine (51 mg) were added, and the mixture was stirred at 80° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the resultant mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant oil was purified by preparative TLC on silica gel (chloroform:methanol=25:1) to obtain the title compound as a hydrochloride.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the residue
  3. washthe resultant mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant oil was purified by preparative TLC on silica gel (chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-4d375eaacbbf42328d35fa5d9a4f573d
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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