Potassium Carbonate → 4-(3-Hydroxypropyl)piperazine-1-carbaldehyde

HRID 2180139Notes

Reaction equation

HRID 2180139 reaction equation
[N:1]1([CH:7]=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:10][CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+]>CO>[OH:13][CH2:12][CH2:11][CH2:10][N:4]1[CH2:5][CH2:6][N:1]([CH:7]=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 224900314-(3-Hydroxypropyl)piperazine-1-carbaldehydeYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-piperazinecarboxaldehyde (25 g, 0.219 mol), 3-bromo-1-propanol (33.5 g, 0.241 mol) and potassium carbonate (38 g, 0.273 mol) in methanol (33 ml) was heated at reflux for 5 hours. After cooling, the solid was filtered, washed with methanol and the filtrate was evaporated. The residue was dissolved in methylene chloride and washed with a small amount of water. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography eluting with methylene chloride/methanol (90/10 followed by 80/20) to give 4-(3-hydroxypropyl)-1-piperazinecarboxaldehyde (4.5 g, 12%).

Workup

  1. temperatureat reflux for 5 hours
  2. temperatureAfter cooling
  3. filtrationthe solid was filtered
  4. washwashed with methanol
  5. customthe filtrate was evaporated
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washwashed with a small amount of water
  8. washThe organic layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by column chromatography
  13. washeluting with methylene chloride/methanol (90/10 followed by 80/20)

Sources & evidence

ORD record
ord-0f76cf9ffcd443af8462e2366a55cc36
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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