Benzaldehyde → HCID 23121885, compound

HRID 1713508Notes

Reaction equation

HRID 1713508 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][NH2:4].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Na+].C(N(CC)CC)C.Br[CH:24]([CH2:30]Br)[C:25]([O:27][CH2:28][CH3:29])=[O:26].[C:32]1([CH3:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(O)C.C(OCC)(=O)C>[C:7]1([CH2:6][N:4]2[CH2:3][CH2:2][CH2:1][N:5]([CH2:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:30][CH:24]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

9

Reactant 6

HCID 240BenzaldehydeHCID 4281,3-PropanediamineHCID 1140TolueneHCID 8471TriethylamineHCID 97945Ethyl 2,3-dibromopropionateHCID 4311764Sodium borohydride

Product 1

HCID 23121885HCID 23121885, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1,3-Propanediamine (50 g, 0.67 mol) was dissolved in ethanol (500 mL), with ice cooling, benzaldehyde (140 g, 1.4 mol) was added thereto, and the mixture was stirred at 70° C. for 2 hours. The reaction solution was concentrated under reduced pressure. To the residue were added methanol (1000 mL) and ethanol (500 mL), with ice cooling, sodium borohydride (61 g, 1.6 mol) was added portionwise thereto over 1 hour, and the mixture was stirred at room temperature overnight. Then, the reaction solution was concentrated under reduced pressure, and water was added to the residue. The reaction solution was extracted with ethyl acetate and washed with an aqueous saturated sodium chloride solution. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain an oily matter (180 g). To 81 g of the obtained oily matter were added toluene (1000 mL), triethylamine (76 g, 0.75 mol) and ethyl 2,3-dibromopropionate (43 mL), and the mixture was stirred at 70° C. overnight. The reaction solution was cooled to room temperature and ethyl acetate was added thereto. The resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=20:1 to hexane:ethyl acetate=9:1) to obtain the title compound (52 g, yield 49%).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionTo the residue were added methanol (1000 mL) and ethanol (500 mL)
  4. waitover 1 hour
  5. stirringthe mixture was stirred at room temperature overnight
  6. concentrationThen, the reaction solution was concentrated under reduced pressure, and water
  7. additionwas added to the residue
  8. extractionThe reaction solution was extracted with ethyl acetate
  9. washwashed with an aqueous saturated sodium chloride solution
  10. dry with materialThe extract was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customto obtain an oily matter (180 g)
  13. stirringthe mixture was stirred at 70° C. overnight
  14. temperatureThe reaction solution was cooled to room temperature
  15. washThe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  16. dry with materialdried over anhydrous magnesium sulfate
  17. concentrationconcentrated under reduced pressure
  18. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=20:1 to hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-59fbbe2c91fa47139c80a72d04c96fc8
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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