Phenethylamine → HCID 4220578, compound

HRID 1030471Notes

Reaction equation

HRID 1030471 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10](O)(=O)[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)O.[OH:21][NH-]>O>[C:3]1([CH:2]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:11][CH2:10][NH:9][C:1]2=[O:21])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 1292Mandelic AcidHCID 178514248HCID 178514248, compound

Product 1

HCID 4220578HCID 4220578, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 31.4 mL of phenethylamine (0.25 mol) and 42.6 g of DL-mandelic acid (0.28 mol, 1.12 eq.) in 600 mL of xylenes was heated to reflux with a Dean-Stark water separator for 8 hr. The reaction was cooled, and the xylenes removed in vacuo. The resulting residue was partitioned between saturated NaHCO3 and CH2Cl2. The CH2Cl12 layer was dried (Na2SO4) and the solvents removed to yield a solid which was recrystallized from THF to yield, after drying, 56 g of hydroxyamide (88%) as a white, crystalline solid, mp 95°-96° (Lit 97°-98° ) To 350 g of PPA at 25° was added 30.7g of this solid (120 mmol) with mechanical stirring. The reaction was heated to 65° for 2 hr, then poured onto ice in a 4L beaker. The resulting suspension was stirred vigorously, the solids pulverized under H2O and filtered, washing well with H2O. Drying of the solid in vacuo and recrystallization from absolute EtOH provided 27 g of 1-phenyl-1,3,4,5-tetrahydro-3(2H)-benzazepin-2-one (95%) as a white solid, mp 189°-191° .

Workup

  1. temperaturewas heated
  2. temperatureThe reaction was cooled
  3. customthe xylenes removed in vacuo
  4. customThe resulting residue was partitioned between saturated NaHCO3 and CH2Cl2
  5. dry with materialThe CH2Cl12 layer was dried (Na2SO4)
  6. customthe solvents removed
  7. customto yield a solid which
  8. customwas recrystallized from THF
  9. customto yield
  10. customafter drying
  11. temperatureThe reaction was heated to 65° for 2 hr
  12. filtrationfiltered
  13. washwashing well with H2O
  14. dry with materialDrying of the solid in vacuo and recrystallization from absolute EtOH

Sources & evidence

ORD record
ord-81aab92c13b34fe285d6f65c887bd3a4
Source dataset
uspto-grants-1992_04
Patent number
US05106844

Reaction notes

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