Water → HCID 19763583, compound

HRID 248473Notes

Reaction equation

HRID 248473 reaction equation
[CH3:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7](=O)[CH:8]=O.[CH2:15]([NH2:18])[CH2:16][NH2:17].[BH4-].[Na+].O>C(O)C.O1CCOCC1>[CH3:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[CH:7]1[CH2:8][NH:18][CH2:15][CH2:16][NH:17]1

Participants

7

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 19763563HCID 19763563, compound

Product 1

HCID 19763583HCID 19763583, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A 5 g portion of the above aldehyde was dissolved in a mixture of 100 ml of ethanol and 10 ml of dioxane. To this mixture, in an ice bath was added a solution of 1.61 g of ethylenediamine in ethanol. The mixture was stirred for one hour at room temperature, recooled to 0°-5° C. and 2.04 g of sodium borohydride added. The mixture was stored at room temperature overnight, water was added and all the solvents were removed. The residue was extracted with dichloromethane, water washed, dried, filtered and evaporated. This residue was purified by flash column chromatography, eluting with chloroform:-methanol (9:1), giving 2.39 g of 2-(3-methylbenzo[b]-thien-2-yl)piperazine.

Workup

  1. customrecooled to 0°-5° C.
  2. waitThe mixture was stored at room temperature overnight
  3. customall the solvents were removed
  4. extractionThe residue was extracted with dichloromethane, water
  5. washwashed
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThis residue was purified by flash column chromatography
  10. washeluting with chloroform

Sources & evidence

ORD record
ord-adbb6ec7b9654d49bb9d1bf8fce374b3
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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