Methanol → 2-[2-(5-Methyl-2-thienyl)ethoxy]ethanamine

HRID 1741446Notes

Reaction equation

HRID 1741446 reaction equation
B.O1CCCC1.[CH3:7][C:8]1[S:12][C:11]([CH2:13][CH2:14][O:15][CH2:16][C:17]([NH2:19])=O)=[CH:10][CH:9]=1.CO>O1CCCC1>[CH3:7][C:8]1[S:12][C:11]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH2:19])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 187790562-[2-(5-Methyl-2-thienyl)ethoxy]acetamide

Product 1

HCID 195934942-[2-(5-Methyl-2-thienyl)ethoxy]ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran solution (1.0 M in THF, 21.7 ml) was added dropwise to a stirred solution of the product from step b) (1.25 g) in dry tetrahydrofuran (100 ml). The reaction was heated at reflux under an inert atmosphere for 5 hours. The reaction was cooled and methanol (10 ml) added cautiously. The solvents were removed in vacuo and the residue dissolved in methanol (100 ml) to which was added concentrated hydrochloric acid (sg. 1.18, 0.45 ml). This solution was heated at reflux for 15 min then the solvent removed in vacuo. The residue was purified by flash chromatography (dichloromethane: 5% methanol as eluant) to give the subtitle compound as a white solid (0.916 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under an inert atmosphere for 5 hours
  3. temperatureThe reaction was cooled
  4. customThe solvents were removed in vacuo
  5. dissolutionthe residue dissolved in methanol (100 ml) to which
  6. additionwas added concentrated hydrochloric acid (sg. 1.18, 0.45 ml)
  7. temperatureThis solution was heated
  8. temperatureat reflux for 15 min
  9. customthe solvent removed in vacuo
  10. customThe residue was purified by flash chromatography (dichloromethane: 5% methanol as eluant)

Sources & evidence

ORD record
ord-03e87028005043d789ccfd0be7af1498
Source dataset
uspto-grants-1999_10
Patent number
US05973167

Reaction notes

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