1-Phenethylamine → HCID 86758413, compound

HRID 2303972Notes

Reaction equation

HRID 2303972 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)CC>[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 53.6%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
90 °C

Procedure

1.21 g (10.0 mmol) of (−)-1-phenylethylamine and 25 ml of 1-propanol were added to 2.77 g (10.0 mmol) of (±)-3-(3,4-dichlorophenyl)-3-methoxycarbonylpropionic acid and dissolved by heating. Then the solution was cooled to an internal temperature of 90° C. and inoculated with the separately prepared seed crystals. The solution was then cooled to an internal temperature of 70 to 72° C. and stirred in a suspended state for 8 hours. Then the solution was further cooled to an internal temperature of 20° C. and stirred at this temperature for 0.5 hour, and the precipitated crystals were filtered out, washed with a small quantity of 1-propanol and dried to obtain 2.13 g (53.6% yield) of (+)-3-(3,4-dichlorophenyl)-3-methoxycarbonylpropionic acid·(S)-1-phenylethylamine salt.

Workup

  1. dissolutiondissolved
  2. temperatureby heating
  3. temperatureThe solution was then cooled to an internal temperature of 70 to 72° C.
  4. temperatureThen the solution was further cooled to an internal temperature of 20° C.
  5. stirringstirred at this temperature for 0.5 hour
  6. filtrationthe precipitated crystals were filtered out
  7. washwashed with a small quantity of 1-propanol
  8. customdried

Sources & evidence

ORD record
ord-144691cd5e714957a2079c8543a6eeb8
Source dataset
uspto-grants-2002_08
Patent number
US06433174B1

Reaction notes

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