Potassium Carbonate → HCID 9875521, compound

HRID 2303350Notes

Reaction equation

HRID 2303350 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[CH:4]=1.[CH3:21][C@H:22]1[CH2:27][NH:26][CH2:25][C@@H:24]([CH3:28])[NH:23]1.[C:29](=[O:32])([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:1].[ClH:1].[ClH:1].[ClH:1].[CH3:20][O:19][C:11]1[CH:10]=[C:9]([C:5]2[CH:4]=[C:3]([CH2:2][N:23]3[C@H:24]([CH3:28])[CH2:25][N:26]([CH2:2][C:3]4[CH:8]=[CH:7][N:6]=[C:5]([C:9]5[CH:10]=[C:11]([O:19][CH3:20])[C:12]([O:17][CH3:18])=[C:13]([O:32][CH3:29])[CH:14]=5)[CH:4]=4)[CH2:27][C@@H:22]3[CH3:21])[CH:8]=[CH:7][N:6]=2)[CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 120192374-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridine

Product 1

HCID 9875521HCID 9875521, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridine (123 mg) and cis-2,6-dimethylpiperazine (23 mg) were dissolved in DMF (5 mL), and to the solution potassium carbonate (58 mg) was added. The mixture was stirred at 80° C. for 4 hours and concentrated under reduced pressure. Water was added to the residue to conduct extraction with chloroform. The resultant organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=40:1) to obtain a free base of the title compound. This compound was dissolved in ethyl acetate, and to the solution an ethyl acetate solution of 4 M hydrogen chloride was added to provide a hydrochloride.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionextraction with chloroform
  4. washThe resultant organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-cdfa757732934e0f88308e109a99b22f
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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