2-(2-Chlorophenoxymethyl)oxirane → N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine hydrochloride

HRID 1656646

Reaction equation

HRID 1656646 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[CH2:3]1.[Cl:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[O:16][CH2:17][CH:18]1[O:20][CH2:19]1>C(O)C>[ClH:13].[OH:12][C:6]1[CH:5]=[C:4]2[C:9]([CH2:10][CH2:11][CH:2]([NH:1][CH2:19][CH:18]([OH:20])[CH2:17][O:16][C:15]3[CH:21]=[CH:22][CH:23]=[CH:24][C:14]=3[Cl:13])[CH2:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 1375002-(2-Chlorophenoxymethyl)oxiraneHCID 109427847-Amino-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 19788315N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine hydrochlorideYield 100.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-7-hydroxytetralin (1.9 g) and 1-(2-chlorophenoxy)-2,3-epoxypropane (2.15 g) in absolute ethanol (60 ml) is refluxed for 5 hours and then ethanol is evaporated off under reduced pressure. The thus obtained residue is chromatographed on a silica gel column eluting first with ethyl acetate up to the complete elution of the first spot and then with a mixture ethyl acetate/methanol 9/1 v/v. The obtained fractions are pooled and concentrated to dryness. The residue is dissolved in isopropanol (20 ml) and the obtained solution is acidified by the addition of HC1/isopropanol. The precipitate is recovered by filtration yielding 2.25 g of N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine hydrochloride; m.p. 201°-203° C.

Workup

  1. temperatureis refluxed for 5 hours
  2. customethanol is evaporated off under reduced pressure
  3. customThe thus obtained residue is chromatographed on a silica gel column
  4. washeluting first with ethyl acetate up to the complete elution of the first spot
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue is dissolved in isopropanol (20 ml)
  7. additionthe obtained solution is acidified by the addition of HC1/isopropanol
  8. filtrationThe precipitate is recovered by filtration

Sources & evidence

ORD record
ord-e098c31bbd3d47c7aca3880fe4654525
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Linked notes

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