Triethylamine → HCID 68526067, compound

HRID 884135Notes

Reaction equation

HRID 884135 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[CH2:35]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)[C:36]1[CH:44]=[CH:43][C:42]2[O:41][CH2:40][O:39][C:38]=2[CH:37]=1>ClCCl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][CH2:20][C:21]([N:48]2[CH2:49][CH2:50][N:45]([CH2:35][C:36]3[CH:44]=[CH:43][C:42]4[O:41][CH2:40][O:39][C:38]=4[CH:37]=3)[CH2:46][CH2:47]2)=[O:23])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 944261-PiperonylpiperazineHCID 68523026HCID 68523026, compound

Product 1

HCID 68526067HCID 68526067, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3-[3-methoxy-4-(5-nitropyridin-2-yloxy)phenyl]propionic acid (3.18 g, 10 mmol) was dissolved in dichloromethane (30 mL). To the resulting solution were added thionyl chloride (0.88 mL, 12 mmol) and DMF (1 drop), and refluxed for 2 hours. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in dichloromethane (20 mL). To the resulting solution were added triethylamine (1.67 mL, 12 mmol) and a solution of 1-piperonylpiperazine (2.20 g, 10 mmol) in dichloromethane (30 mL) under ice cooling, and the resulting solution was stirred for 1 hour at 0° C. The resulting reaction solution was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was recrystallized from ethyl acetate, to thereby yield 4.95 g of the title compound.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (20 mL)
  4. customThe resulting reaction solution
  5. washwas washed with water and brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4a100869baaa44ee940b6384b5dcc1a9
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

Loading…