Ethylenediamine → HCID 19763570, compound

HRID 248491Notes

Reaction equation

HRID 248491 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[CH:5][C:6]=1[C:7](=O)[CH:8]=O.[CH2:12]([NH2:15])[CH2:13][NH2:14].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[CH:5][C:6]=1[CH:7]1[CH2:8][NH:15][CH2:12][CH2:13][NH:14]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 19763549HCID 19763549, compound

Product 1

HCID 19763570HCID 19763570, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 10.45 g portion of the above aldehyde was suspended in 200 ml of ethanol, cooled to 0°-5° C. and a solution of 3.3 g of ethylenediamine in 20 ml of ethanol added dropwise with stirring. The mixture was allowed to ccme to room temperature over 3 hours, then 3.8 g of sodium borohydride was added and the mixture was evaporated to dryness. The residue was dissolved in dichloromethane, water washed, filtered, dried and evaporated. The resulting gum was triturated with ether producing an oil. The oil was purified by chromatography, eluting with chloroform:methanol (9:1), giving an oil which crystallized, giving 3.3 g of 2-(2,5-dichloro-3-thienyl)piperazine.

Workup

  1. temperaturecooled to 0°-5° C.
  2. customthe mixture was evaporated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwater washed
  5. filtrationfiltered
  6. customdried
  7. customevaporated
  8. customThe resulting gum was triturated with ether producing an oil
  9. customThe oil was purified by chromatography
  10. washeluting with chloroform:methanol (9:1)
  11. customgiving an oil which
  12. customcrystallized

Sources & evidence

ORD record
ord-a733bb8496044e27a89100575d403b99
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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