1,2,3,4-Tetrahydro-1-naphthylamine → HCID 67871619, compound

HRID 1656648Notes

Reaction equation

HRID 1656648 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.[OH:12][C@H:13]1[C@H:22]([OH:23])[CH2:21][C:20]2[C:19]([O:24][CH2:25][CH:26]3[O:28][CH2:27]3)=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:14]1>C(O)C>[CH:2]1([NH:1][CH2:27][CH:26]([OH:28])[CH2:25][O:24][C:19]2[C:20]3[CH2:21][C@@H:22]([OH:23])[C@H:13]([OH:12])[CH2:14][C:15]=3[CH:16]=[CH:17][CH:18]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 12445770HCID 12445770, compound

Product 1

HCID 67871619HCID 67871619, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-aminotetralin (0.8 g) and 1-[(trans-6,7-dihydroxy-5,6,7,8-tetrahydronaphth-1-yl)oxy]-2,3-epoxypropane (1.3 g), prepared by the method described in J. Med. Chem., 1978, 21, No. 9, 913-922, in absolute ethanol (20 ml) is refluxed for 5 hours and the solvent is then evaporated off. The residue is chromatographed on a silica gel column eluting first with ethyl acetate and then with a mixture ethyl acetate/methanol 7/3 v/v. The combined fractions are evaporated to dryness yielding 1.0 g of N-(1,2,3,4-tetrahydronaphth-1-yl)-2-hydroxy-3-(trans-6,7-dihydroxy-5,6,7,8-tetrahydronaphth-1-yloxy)propanamine as a vitreous solid.

Workup

  1. customprepared by the method
  2. customthe solvent is then evaporated off
  3. customThe residue is chromatographed on a silica gel column
  4. washeluting first with ethyl acetate
  5. customThe combined fractions are evaporated to dryness

Sources & evidence

ORD record
ord-686f786f0a9a4f719f2a03102245ca13
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Reaction notes

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