1,2,3,4-Tetrahydro-1-naphthylamine → N-(1,2,3,4-tetrahydronaphth-l-yl)-2-hydroxy-3-(4-indolyloxy)propanamine

HRID 1656612Notes

Reaction equation

HRID 1656612 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.C1(C)C=CC(S([N:21]2[C:29]3[C:24](=[C:25]([O:30][CH2:31][CH:32]4[O:34][CH2:33]4)[CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)(=O)=O)=CC=1>C(O)C.C(OCC)(=O)C>[CH:2]1([NH:1][CH2:33][CH:32]([OH:34])[CH2:31][O:30][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:24]=2[CH:23]=[CH:22][NH:21]3)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 13938676glycidyl N-tosyl-4-indolyl ether

Product 1

HCID 14750931N-(1,2,3,4-tetrahydronaphth-l-yl)-2-hydroxy-3-(4-indolyloxy)propanamineYield 12.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-aminotetralin (5.15 g) and 1-[1-(p-toluenesulfonyl)indol-4-yloxy]-2,3-epoxypropane (12 g) in absolute ethanol (150 ml) is refluxed for 6 hours. The solvent is then evaporated off and the oily residue is dissolved in absolute ethanol (100 ml). A solution of sodium hydroxide (7.5 g) in water (30 ml) is added thereto. The obtained reaction mixture is refluxed for 6 hours and then evaporated under reduced pressure. The residue which is obtained is then dissolved in ethyl acetate (150 ml), the organic solution is thoroughly washed with water, dried over sodium sulfate, and filtered. Ethyl acetate is then evaporated off and the obtained oily residue is chromatographed on a silica gel column eluting with a mixture ethyl acetate/cyclohexane 7/3 v/v. The combined fractions are evaporated to dryness, the oily residue is taken up in a very small amount of ethyl ether which is then removed under vacuum yielding 1.5 g of N-(1,2,3,4-tetrahydronaphth-l-yl)-2-hydroxy-3-(4-indolyloxy)propanamine, as a vitreous solid.

Workup

  1. temperatureis refluxed for 6 hours
  2. customThe solvent is then evaporated off
  3. dissolutionthe oily residue is dissolved in absolute ethanol (100 ml)
  4. additionA solution of sodium hydroxide (7.5 g) in water (30 ml) is added
  5. customThe obtained reaction mixture
  6. temperatureis refluxed for 6 hours
  7. customevaporated under reduced pressure
  8. customThe residue which is obtained
  9. washthe organic solution is thoroughly washed with water
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customEthyl acetate is then evaporated off
  13. customthe obtained oily residue is chromatographed on a silica gel column
  14. washeluting with a mixture ethyl acetate/cyclohexane 7/3 v/v
  15. customThe combined fractions are evaporated to dryness
  16. customis then removed under vacuum

Sources & evidence

ORD record
ord-53597fdedb0b4768898662aebc5eeb06
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Reaction notes

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