Triethylamine → HCID 57430050, compound

HRID 2354587Notes

Reaction equation

HRID 2354587 reaction equation
[C:1]1([CH:7]([CH3:11])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].CCN(CC)CC>ClCCCl.CN(C=O)C.CCOCC>[C:1]1([CH:7]([CH3:11])[C:8]([N:26]2[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 102962-Phenylpropionic acidHCID 24386Thionyl ChlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 57430050HCID 57430050, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 2-phenyl propionic acid (1.0 g, 6.7 mmol) in 1,2-dichloroethane (15 mL) was added a few drops of DMF and excess thionyl chloride. The resulting mixture was heated at reflux for 2 h, when bubbling ceased the mixture was evaporated to dryness. The crude residue was co-evaporated with toluene and 1,2-dichloroethane. The residue was dissolved in CH2Cl2 and cooled to 0° C. To the stirred solution, BOC-piperazine (1.24 g, 6.7 mmol) and Et3N were added. A white precipitate formed and the reaction was stirred 12 h at RT. Et2O was added and the mixture was washed with water and brine. The ether layer was separated and dried over anhydrous Na2SO4, filtered, and evaporated. The residue was treated with 20% ether/hexanes and the resulting solid filtered. The filtrate was evaporated and the procedure repeated. After drying, there remained a white solid (1.3 g, 62%). 1H NMR (CDCl3) δ: 1.4 (s, 9H), 1.42 (d, 3H), 2.7 (m, 1H), 3.1-3.6 (m, 6H), 3.85 (m, 2H), 7.2-7.4 (m, 5H). [M+Na] 341.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 h
  3. customwhen bubbling
  4. customwas evaporated to dryness
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. customA white precipitate formed
  7. washthe mixture was washed with water and brine
  8. customThe ether layer was separated
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. customevaporated
  12. additionThe residue was treated with 20% ether/hexanes
  13. filtrationthe resulting solid filtered
  14. customThe filtrate was evaporated
  15. customAfter drying

Sources & evidence

ORD record
ord-43b63ad9d9a641028f99f47f6a56a9bf
Source dataset
uspto-grants-2010_07
Patent number
US07754724B2

Reaction notes

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