Propylamine → HCID 10469743, compound

HRID 1173314Notes

Reaction equation

HRID 1173314 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([C:10]([Cl:14])=[C:11]([Cl:13])[Cl:12])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:15]([NH2:18])[CH2:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[CH2:15]([NH:18][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([C:10]([Cl:14])=[C:11]([Cl:13])[Cl:12])=[CH:9][C:2]=1[OH:1])[CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 7852PropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86601164HCID 86601164, compound

Product 1

HCID 10469743HCID 10469743, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.211 g (0.84 mmol) of the product of Step A and 0.177 g (2.94 mmol) of n-propylamine dissolved in 8 mL of CH2Cl2 was added 0.5 g of finely powdered 4 Å molecular sieves. The reaction mixture was stirred under a nitrogen atmosphere at room temperature overnight, then 0.445 g (2.1 mmol) of sodium triacetoxyborohydride was added. The reaction was then stirred an addition 8 h at room temperature, then diluted with CH2Cl2 and MeOH. The mixture was filtered through a pad of Celite filter aid eluted with CH2Cl2, and the filtrate was washed with saturated aqueous NaHCO3. The organic layer was the separated, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted first with CH2Cl2-MeOH—NH4OH (96:3:1) followed by CH2Cl2-MeOH—NH4OH (94:5:1). Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. additionwas added 0.5 g of finely powdered 4 Å molecular sieves
  2. stirringThe reaction was then stirred
  3. additionan addition 8 h at room temperature
  4. filtrationThe mixture was filtered through a pad of Celite
  5. filtrationfilter aid
  6. washeluted with CH2Cl2
  7. washthe filtrate was washed with saturated aqueous NaHCO3
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue was purified on a silica gel flash chromatography column
  12. washeluted first with CH2Cl2-MeOH—NH4OH (96:3:1)
  13. customEvaporation of the purified fractions
  14. customdrying in vacuo

Sources & evidence

ORD record
ord-8d6cc38983884c96b50c40e8cc931cdf
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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