1-Phenethylamine, (-)- → 1-Phenethylamine, (-)-

HRID 1003282Notes

Reaction equation

HRID 1003282 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([CH:13]([OH:17])[C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([C@@H:26]([NH2:28])[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO.C(OCC)(=O)C>[C:20]1([C@@H:26]([NH2:28])[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([C@H:13]([OH:17])[C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 140103192-(4-(Benzyloxy)phenyl)-2-hydroxyacetic acid

Product 2

HCID 758181-Phenethylamine, (-)-HCID 54160087HCID 54160087, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

4-Benzyloxymandelic acid (40.8 g) was dissolved in methanol (405 ml) and ethyl acetate (405 ml), and a solution of (S)-1-phenylethylamine (20.4 ml) in methanol (200 ml) and ethyl acetate (200 ml) was added to the solution. After the mixture was allowed to stand at room temperature, the resulting precipitates (37.9 g) were obtained. Recrystallization of the precipitates from methanol (926 ml) gave a salt of (S)-1-phenylethylamine and (S)-4-benzyloxymandelic acid (24.8 g) having a melting point of 174-180° C.

Workup

  1. customto stand at room temperature
  2. customthe resulting precipitates (37.9 g)
  3. customwere obtained
  4. customRecrystallization of the
  5. customprecipitates from methanol (926 ml)

Sources & evidence

ORD record
ord-75cbbb07076647a6a1c67e8e1593d7e5
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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