Water → 2-(3-Methylthiophen-2-YL)piperazine

HRID 2165615Notes

Reaction equation

HRID 2165615 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=O)[CH:8]=O.[CH2:11]([NH2:14])[CH2:12][NH2:13].[BH4-].[Na+].O>C(O)C>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:8][NH:14][CH2:11][CH2:12][NH:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 230429823-Methyl-alpha-oxo-2-thiopheneacetaldehyde

Product 1

HCID 197635922-(3-Methylthiophen-2-YL)piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 5 g portion of the above aldehyde was dissolved in 100 ml of ethanol, cooled to 0°-5° C. and a solution of 2.14 g of ethylenediamine in 10 ml of ethanol was added dropwise with stirring. The mixture was allowed to come to room temperature over 3 hours, then 2.4 g of sodium borohydride was added and the mixture was stirred for 18 hours. Water was added, then the mixture was concentrated. The residue was dissolved in dichloromethane, cooled, extracted with water, dried, filtered and evaporated to an oil which crystallized, giving 4.6 g of 2-(3-methyl-2-thienyl)piperazine.

Workup

  1. temperaturecooled to 0°-5° C.
  2. stirringthe mixture was stirred for 18 hours
  3. concentrationthe mixture was concentrated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. temperaturecooled
  6. extractionextracted with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated to an oil which
  10. customcrystallized

Sources & evidence

ORD record
ord-b4635049c3d740aca719e174b0674c49
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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