2-Aminotetralin → N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-naphthyloxy)propanamine

HRID 1656643

Reaction equation

HRID 1656643 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH:13]1[O:15][CH2:14]1.[NH2:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1>C(O)C>[CH2:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:25][CH2:26][CH:17]1[NH:16][CH2:14][CH:13]([OH:15])[CH2:12][O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

4

Reactant 2

HCID 346772-AminotetralinHCID 929952-Naphthyl glycidyl ether

Product 1

HCID 19788252N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-naphthyloxy)propanamineYield 53.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(2-naphthyloxy)-2,3-epoxypropane (1.95 g), 2-aminotetralin (2.65 g) and ethanol (35 ml) is heated to the reflux temperature for 5 hours. The solvent is then evaporated off and the thus obtained solid residue is crystallized from ethyl acetate (5 ml), recovered by filtration, washed with ethyl acetate and then with ethyl ether, and dried yielding 1.8 g of N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-naphthyloxy)propanamine, as the free base; m.p. 102°-115° C.

Workup

  1. temperatureis heated to the reflux temperature for 5 hours
  2. customThe solvent is then evaporated off
  3. customthe thus obtained solid residue is crystallized from ethyl acetate (5 ml)
  4. filtrationrecovered by filtration
  5. washwashed with ethyl acetate
  6. dry with materialwith ethyl ether, and dried

Sources & evidence

ORD record
ord-6d61e845ef5d45ed9a722e30b04140de
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Linked notes

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