Diethyl Ether → HCID 19770998, compound

HRID 1589833Notes

Reaction equation

HRID 1589833 reaction equation
I.CS[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]=1.[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.CCOCC>C(O)C>[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][CH2:6][N:5]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 974724-HydroxybenzylamineHCID 19771018HCID 19771018, compound

Product 1

HCID 19770998HCID 19770998, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Methylthio-3,4-dihydroisoquinoline hydroiodide (0.6 g, 0.00197 mol) and 4-hydroxybenzylamine (0.24 g, 0.00195 mol) were heated together at reflux temperature in ethanol (25 ml) for five hours. Effluent gases were passed through a CHLOROS trap. The mixture was then cooled and the ethanol evaporated off at reduced pressure. The tacky residue was dissolved in dilute HCl and the solution extracted with ethyl acetate. The clear aqueous solution was basified with 6N. NaOH and re-extracted with ethyl acetate. The latter organic extract was washed with water, dried and evaporated to dryness to give a white sticky solid. This was treated with ether and the ether decanted off. The residual solid was crystallised from absolute ethanol to give the title compound (0.11 g) as white crystals, m.p. 177°-179°.

Workup

  1. customEffluent gases were passed through a CHLOROS trap
  2. temperatureThe mixture was then cooled
  3. customthe ethanol evaporated off at reduced pressure
  4. dissolutionThe tacky residue was dissolved in dilute HCl
  5. extractionthe solution extracted with ethyl acetate
  6. extractionNaOH and re-extracted with ethyl acetate
  7. extractionThe latter organic extract
  8. washwas washed with water
  9. customdried
  10. customevaporated to dryness
  11. customto give a white sticky solid
  12. customthe ether decanted off
  13. customThe residual solid was crystallised from absolute ethanol

Sources & evidence

ORD record
ord-45f2fec405024cb99b5290c1e90e1be3
Source dataset
uspto-grants-1993_04
Patent number
US05200417

Reaction notes

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