1-Phenethylamine → HCID 86758413, compound

HRID 2303973Notes

Reaction equation

HRID 2303973 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]>CC(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 84.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
20 °C

Procedure

1.22 g (10.1 mmol) of (−)-1-phenylethylamine, 0.0766 g (0.503 mmol) of 1,8-diazobicyclo[5.4.0]-undeca-7-ene (hereinafter abbreviated as DBU) and 23.9 ml of 2-propanol were added to 2.77 g (10.0 mmol) of (±)-3-(3,4-dichlorophenyl)-3-methoxycarbonylpropionic acid and heated until the internal temperature became 72° C. With this temperature maintained, the solution was stirred in a suspended state for 8 hours, then it was cooled to an internal temperature of 20° C. and further stirred at this temperature for 0.5 hour. The precipitated crystals were filtered out, washed with a small amount of 2-propanol and dried to obtain 3.37 g (84.7% yield) of (+)-3-(3,4-dichlorophenyl)-3-methoxycarbonylpropionic acid·(S)-1-phenylethylamine salt.

Workup

  1. temperatureheated until the internal temperature
  2. custombecame 72° C
  3. temperatureWith this temperature maintained
  4. stirringfurther stirred at this temperature for 0.5 hour
  5. filtrationThe precipitated crystals were filtered out
  6. washwashed with a small amount of 2-propanol
  7. customdried

Sources & evidence

ORD record
ord-a7d90651ec94401f9f42bd83c8de49f9
Source dataset
uspto-grants-2002_08
Patent number
US06433174B1

Reaction notes

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