Propanal → HCID 86750388, compound

HRID 1451772Notes

Reaction equation

HRID 1451772 reaction equation
[CH:1](=O)[CH2:2][CH3:3].[NH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=3)[CH:13]=2)[CH2:8]1.[BH4-].[Na+]>CO>[CH2:1]([CH:8]1[CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[C:12]([C:16]3[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=3)[CH:11]=2)[CH:7]1[CH2:6][NH2:5])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 527PropanalHCID 4311764Sodium borohydrideHCID 21476304HCID 21476304, compound

Product 1

HCID 86750388HCID 86750388, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Propanal (1.51 g) dissolved in 5 ml of methanol was added dropwise to 6.15 g of 2-aminomethyl-5-[4,5-dihydro-pyridazin-3(2H)-on-6-yl]indane dissolved in 60 ml of methanol. The mixture was stirred at room temperature for 30 minutes. Then, under ice cooling, 1.03 g of sodium borohydride was added to the mixture. The resulting mixture was stirred at the same temperature for 20 minutes and then stirred at room temperature for 1 hour. After methanol was removed, water was added to the residue, and the residue was extracted with ethyl acetate. The organic layer was collected by filtration, washed with water and dried, and the solvent was removed. The residue was purified by silica gel column chromatography (solvent; chloroform: methanol (15:1)) to obtain 5.22 g of 2-propyl-aminomethyl-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane.

Workup

  1. stirringThe resulting mixture was stirred at the same temperature for 20 minutes
  2. stirringstirred at room temperature for 1 hour
  3. customAfter methanol was removed
  4. additionwater was added to the residue
  5. extractionthe residue was extracted with ethyl acetate
  6. filtrationThe organic layer was collected by filtration
  7. washwashed with water
  8. customdried
  9. customthe solvent was removed
  10. customThe residue was purified by silica gel column chromatography (solvent; chloroform: methanol (15:1))

Sources & evidence

ORD record
ord-6fcda02b438c4904aace4c2ad43b59e1
Source dataset
uspto-grants-1997_02
Patent number
US05605901

Reaction notes

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