1-Phenethylamine, (-)- → HCID 59492949, compound

HRID 1799034Notes

Reaction equation

HRID 1799034 reaction equation
[Cl:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([OH:19])([C:15]([F:18])([F:17])[F:16])[C:6]=2[CH:5]=[C:4]([C:20]([OH:22])=[O:21])[CH:3]=1.[C:23]1([C@@H](N)C)C=CC=CC=1>C(OCC)(=O)C>[CH3:23][O:21][C:20]([C:4]1[CH:3]=[C:2]([Cl:1])[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([OH:19])([C:15]([F:17])([F:18])[F:16])[C:6]=2[CH:5]=1)=[O:22]

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 59492938HCID 59492938, compound

Product 1

HCID 59492949HCID 59492949, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-chloro-9-hydroxy-9-trifluoromethyl-9H-fluorene-2-carboxylic acid (0.050 g) and isopropyl ether (0.250 ml) was added (S)-(−)-1-phenylethylamine (0.020 ml), and the mixture was stirred at room temperature overnight. This suspension was filtered to give a solid (0.060 g). The solid was added as a seed crystal to a mixture of 4-chloro-9-hydroxy-9-trifluoromethyl-9H-fluorene-2-carboxylic acid (0.050 g), (S)-(−)-1-phenylethylamine (0.020 ml) and ethyl acetate (0.250 ml), which had been stirred overnight at room temperature in advance, and the mixture was further stirred at room temperature overnight. The resulting suspension was filtered, and the obtained solid was washed with ethyl acetate. The solid was dried under reduced pressure to give the title compound (0.019 g). The solid was analyzed under HPLC analysis condition 4 to find that an isomer with a long retention time was the main component.

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. filtrationThe resulting suspension was filtered
  3. washthe obtained solid was washed with ethyl acetate
  4. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-0387375f64a24cda9690c535b2e6f37d
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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