Potassium Carbonate → HCID 71061815, compound

HRID 1774313Notes

Reaction equation

HRID 1774313 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[C:20]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:21][CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[O:4][CH2:3][CH2:2][N:28]1[CH2:29][CH2:30][N:25]([C:20]2[C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=3)=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122988871-(2-CHLOROETHOXY)-3-METHOXYBENZENEHCID 71061917HCID 71061917, compound

Product 1

HCID 71061815HCID 71061815, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 1-(2-chloroethoxy)-3-methoxybenzene (0.65 g, 3.5 mmol), 1-[3-(2-pyridyl)-2-pyridyl]piperazine (0.7 g, 2.9 mmol) and K2CO3 (3.5 mmol) in DMF was refluxed overnight. After cooling, the mixture was evaporated to dryness and H2O (20 mL) was added to the residue. The aqueous phase was extracted with AcOEt (2×30 mL). The collected organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (CHCl3/AcOEt, 9:1, as eluent) to afford pure compound in 77% yield.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness and H2O (20 mL)
  4. additionwas added to the residue
  5. extractionThe aqueous phase was extracted with AcOEt (2×30 mL)
  6. dry with materialThe collected organic layers were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe crude residue was chromatographed (CHCl3/AcOEt, 9:1, as eluent)
  9. customto afford pure compound in 77% yield

Sources & evidence

ORD record
ord-0ffb302513424390a0d2b06087c04010
Source dataset
uspto-grants-2016_02
Patent number
US09260400B2

Reaction notes

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