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

HRID 1656645Notes

Reaction equation

HRID 1656645 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[O:8][CH2:7]1.[NH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1>C(O)C>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:23][CH:14]1[NH:13][CH2:7][CH:6]([OH:8])[CH2:5][O:4][C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 346772-AminotetralinHCID 1375002-(2-Chlorophenoxymethyl)oxirane

Product 1

HCID 19788317N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamineYield 31.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2-chlorophenoxy)-2,3-epoxypropane (2.65 g) prepared by the method described in British Patent 767,991, and 2-aminotetralin (2.1 g) in ethanol (70 ml) is heated to the reflux temperature for 5 hours. Ethanol is then evaporated off and the thus obtained residue is chromatographed on a silica gel column eluting with ethyl acetate. The residue which is obtained upon evaporation to dryness of the combined fractions is crystallized from ethyl acetate (10 ml) yielding 1.5 g of N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine; m.p. 98°-101° C.

Workup

  1. temperatureis heated to the reflux temperature for 5 hours
  2. customEthanol is then evaporated off
  3. customthe thus obtained residue is chromatographed on a silica gel column
  4. washeluting with ethyl acetate
  5. customThe residue which is obtained upon evaporation to dryness of the combined fractions
  6. customis crystallized from ethyl acetate (10 ml)

Sources & evidence

ORD record
ord-96e97f5b438247e98e11ec0771cdc49e
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Reaction notes

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