1-Phenethylamine → HCID 86758413, compound

HRID 2303971Notes

Reaction equation

HRID 2303971 reaction equation
[C:1]1([CH:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]([C:23]([O:25][CH3:26])=[O:24])[CH2:19][C:20]([OH:22])=[O:21])[CH:14]=[CH:15][C:16]=1[Cl:17]>C(O)C>[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]([C:23]([O:25][CH3:26])=[O:24])[CH2:19][C:20]([OH:22])=[O:21])[CH:14]=[CH:15][C:16]=1[Cl:17].[C:1]1([C@@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 74081-PhenethylamineHCID 15524254HCID 15524254, compound

Product 1

HCID 86758413HCID 86758413, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

1.21 g (10.0 mmol) of (−)-1-phenylethylamine and 20 ml of ethanol were added to 2.77 g (10.0 mmol) of (±)-3-(3,4-dichlorophenyl)-3-methoxycarbonylpropionic acid, and the mixture was stirred in a suspended state under heating at a bath temperature of 90 to 110° C. for 4 hours. Then the internal temperature was lowered to 20° C. and the suspension was stirred at this temperature for one hour. The precipitated crystals were filtered out, washed with a small quantity of ethanol and dried to harvest 2.70 g (68.0% yield) of (+)-3-(3,4-dichlorophenyl)-3-methoxycarbonylpropionic acid·(S)-1-phenylethylamine salt.

Workup

  1. customwas lowered to 20° C.
  2. stirringthe suspension was stirred at this temperature for one hour
  3. filtrationThe precipitated crystals were filtered out
  4. washwashed with a small quantity of ethanol
  5. customdried

Sources & evidence

ORD record
ord-d5cf59a237514a109eb4ffec4731a771
Source dataset
uspto-grants-2002_08
Patent number
US06433174B1

Reaction notes

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