2-((1-Naphthalenyloxy)methyl)oxirane → N-(6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(1-naphthyloxy)propanamine

HRID 1656611Notes

Reaction equation

HRID 1656611 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[CH2:3]1.[C:13]1([O:23][CH2:24][CH:25]2[O:27][CH2:26]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>C(O)C>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH2:3][CH:2]([NH:1][CH2:26][CH:25]([OH:27])[CH2:24][O:23][C:13]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=1)[CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 131778796-Amino-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 14750926N-(6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(1-naphthyloxy)propanamineYield 32.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-amino-6-hydroxytetralin (2.6 g) and 1-naphthyloxy-2,3-epoxypropane (3.2 g) in ethanol (80 ml) is refluxed for 5 hours, and then allowed to cool to room temperature. The solvent is evaporated off under reduced pressure and the thus obtained oil is chromatographed on a silica gel column eluting first with ethyl acetate up to complete elution of the first spot, and then with a mixture ethyl acetate/reethanol 9/1 v/v up to complete elution of the product. The fractions are pooled and concentrated under reduced pressure. The residue is dissolved in isopropanol (20 ml) and a solution of fumaric acid (0.95 g) in isopropanol (10 ml) is then added thereto. The precipitate is recovered by filtration, washed with ethyl ether and dissolved in water. A concentrated sodium hydroxide solution is then added thereto up to a basic pH and the solution is extracted with ethyl acetate. The organic extract is dried over sodium sulfate and concentrated to dryness. The residue is triturated with a small amount of ethyl acetate and filtered yielding 1.9 g of N-(6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(1-naphthyloxy)propanamine; m.p. 118°-120° C.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. customthe thus obtained oil is chromatographed on a silica gel column
  3. washeluting first with ethyl acetate up
  4. washelution of the first spot
  5. washelution of the product
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue is dissolved in isopropanol (20 ml)
  8. additiona solution of fumaric acid (0.95 g) in isopropanol (10 ml) is then added
  9. filtrationThe precipitate is recovered by filtration
  10. washwashed with ethyl ether
  11. dissolutiondissolved in water
  12. additionA concentrated sodium hydroxide solution is then added
  13. extractionup to a basic pH and the solution is extracted with ethyl acetate
  14. extractionThe organic extract
  15. dry with materialis dried over sodium sulfate
  16. concentrationconcentrated to dryness
  17. customThe residue is triturated with a small amount of ethyl acetate
  18. filtrationfiltered

Sources & evidence

ORD record
ord-5326529d2d4645a397a4e2ef4a9957c9
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Reaction notes

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