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

HRID 2165626Notes

Reaction equation

HRID 2165626 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-073b5461112542e492346b68aa6da08f
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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