Triethylamine → HCID 131720324, compound

HRID 2294123Notes

Reaction equation

HRID 2294123 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+].[C:36]([O-])(=[S:38])[CH3:37].[K+]>C(Cl)Cl.CN(C=O)C.[I-].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:36](=[S:38])[CH3:37])[CH2:13][CH2:14]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4109013-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-olHCID 516892Sodium BicarbonateHCID 23670855Potassium ethanethioate

Product 1

HCID 131720324HCID 131720324, compoundYield 53.5%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-[4-(2-methoxyphenyl)piperazin-1-yl]-1-propanol (2.16 g, 8.6 mmol), prepared as in Example 10, in 20 mL of methylene chloride was cooled to 0° C. under nitrogen and triethylamine (1.45 mL, 10.5 mmol) and methanesulfonyl chloride (0.74 mL, 9.5 mmol) in 20 mL of methylene chloride were added. The mixture was allowed to warm to room temperature and stirred for 45 minutes. The mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with brine, dried (K2CO3) and concentrated by rotary evaporation. The residue was dissolved in 10 mL of DMF and the solution was added to a mixture of potassium thioacetate (1.18 g, 10.3 mmol) and sodium iodide (65 mg, 0.4 mmol) in 20 mL of DMF. The mixture was purged with nitrogen under a vacuum and then heated at 50° C. for 20 hours. The mixture was allowed to cool to room temperature and partitioned between water and hexanes/ethyl acetate (1:1). The organic layer was separated, washed with water and then brine, dried (Na2SO4) and concentrated. The residue was purified on silica gel by column chromatography eluting with hexanes/ethyl acetate (2:1) to give 3-[4-(2-methoxyphenyl)piperazin-1-yl]propylthioacetate (1.43 g, 4.6 mmol).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated by rotary evaporation
  5. dissolutionThe residue was dissolved in 10 mL of DMF
  6. customThe mixture was purged with nitrogen under a vacuum
  7. temperatureheated at 50° C. for 20 hours
  8. temperatureto cool to room temperature
  9. custompartitioned between water and hexanes/ethyl acetate (1:1)
  10. customThe organic layer was separated
  11. washwashed with water
  12. dry with materialbrine, dried (Na2SO4)
  13. concentrationconcentrated
  14. customThe residue was purified on silica gel by column chromatography
  15. washeluting with hexanes/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-0f6e4019881b44c9a365f9069c7ede63
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

Loading…