Triethylamine → HCID 69848839, compound

HRID 352218

Reaction equation

HRID 352218 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5](Br)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CCN(CC)CC>ClCCl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetate

Product 1

HCID 69848839HCID 69848839, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromo-pyridin-3-yl-acetic acid ethyl ester (2.54 g; 10.2 mmol), was reacted in refluxing dichloromethane, overnight with 1-methylpiperazine (4.54 mL; 41.0 mmol; 4 equiv) and Et3N (5.8 mL; 41.0 mmol; 4 equiv). The reaction solution was evaporated to dryness, dissolved in CH2Cl2, washed five times with saturated NaHCO3 (aq), washed once with saturated NaCl (aq), dried with Na2SO4, filtered, and concentrated in vacuo. The resulting brown oil was purified with silica gel chromatography in a 3×17 cm glass column using a 2% methanol/chloroform (v/v) mobile phase. A second column eluted with 30% EtOAc/hexanes (v/v) followed by a step gradient of 0.5-3% methanol/CH2Cl2 (v/v) produced the desired product as a yellow oil (756 mg; 28% yield). MS(ES) calc'd: [M+H]+=263.1 m/z. Found: 263.1 m/z.

Workup

  1. customThe reaction solution was evaporated to dryness
  2. dissolutiondissolved in CH2Cl2
  3. washwashed five times with saturated NaHCO3 (aq)
  4. washwashed once with saturated NaCl (aq)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting brown oil was purified with silica gel chromatography in a 3×17 cm glass column
  9. washA second column eluted with 30% EtOAc/hexanes (v/v)

Sources & evidence

ORD record
ord-9551cb8e243a4eeca923e0326e56a426
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

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