Triethylamine → HCID 46240533, compound

HRID 244388Notes

Reaction equation

HRID 244388 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1)(=O)=O.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:10]([NH:9][CH2:8][CH2:7][CH2:6][N:32]3[CH2:31][CH2:30][N:29]([C:26]4[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=4)[CH2:34][CH2:33]3)=[CH:11][CH:12]=[N:13]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2697221-(4-Methoxyphenyl)piperazineHCID 516892Sodium BicarbonateHCID 16083007HCID 16083007, compound

Product 1

HCID 46240533HCID 46240533, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Preparation 2 (0.69 g, 0.00219 mol) and 1-(4-methoxyphenyl)piperazine (0.51 g, 0.00263 mol) were dissolved in THF (15 mL) and triethylamine (0.44 g, 0.00438 mol) was added. The reaction mixture was stirred and heated at reflux for 4 days. After cooling to room temperature, saturated NaHCO3 solution (30 mL) was added, and the mixture was extracted with chloroform (3×10 ml). The organic layer was dried over MgSO4 and evaporated. The resulting powder was dissolved in a mixture of methanol/ethyl acetate (1:3) (10 ml). After filtering, the solution was evaporated to give the title compound (0.09 g, 10%) as a solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 days
  3. extractionthe mixture was extracted with chloroform (3×10 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. dissolutionThe resulting powder was dissolved in a mixture of methanol/ethyl acetate (1:3) (10 ml)
  7. filtrationAfter filtering
  8. customthe solution was evaporated

Sources & evidence

ORD record
ord-5580feb0dc214a9b804c33cf0690c5c9
Source dataset
uspto-grants-2014_02
Patent number
US08658648B2

Reaction notes

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