Ethylenediamine → 2-(Furan-2-yl)piperazine

HRID 248480Notes

Reaction equation

HRID 248480 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].O=[C:6]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)[CH:7]=O.[BH4-].[Na+]>C(O)C>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[CH:6]1[CH2:7][NH:4][CH2:1][CH2:2][NH:3]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 1463252-Furanacetaldehyde, alpha-oxo-, hydrateHCID 4311764Sodium borohydride

Product 1

HCID 167407772-(Furan-2-yl)piperazineYield 57.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 10.25 g of ethylene diamine in 250 ml of ethanol was added to a solution of 19.53 g of the above aldehyde in 250 ml of ethanol at 0° C. The mixture was stirred at room temperature for 1.5 hours, then recooled to 0° C. and 9.6 g of sodium borohydride added. This mixture was stirred overnight, quenched with water and the ethanol removed. The residue was extracted with dichloromethane, washed with water, dried and the solvent evaporated. The residue was crystallized from hexaneether, giving 13.8 g of 2-(2-furanyl)piperazine.

Workup

  1. customrecooled to 0° C.
  2. stirringThis mixture was stirred overnight
  3. customquenched with water
  4. customthe ethanol removed
  5. extractionThe residue was extracted with dichloromethane
  6. washwashed with water
  7. customdried
  8. customthe solvent evaporated
  9. customThe residue was crystallized from hexaneether

Sources & evidence

ORD record
ord-4c3c5f475be34fc6845238b9257517ca
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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