Phosphorus oxide (P4O10) → HCID 59396590, compound

HRID 2383031Notes

Reaction equation

HRID 2383031 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=O)=[CH:5][CH:4]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH:14]1([C:12]2[C:7]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=3)[CH2:9][CH2:10][N:11]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 874953HCID 874953, compound

Product 1

HCID 59396590HCID 59396590, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[2-(4-methoxyphenyl)ethyl]cyclohexanecarboxamide (5.56 g) was dissolved in toluene (120 mL), and diphosphorus pentoxide (3.0 g) and phosphorus oxychloride (6.0 mL) were sequentially added thereto, followed by stirring under heating at reflux for 5.5 hours. The reaction mixture was left to cool and then the solvent was evaporated. An aqueous 8 M potassium hydroxide solution, water and chloroform were added to the resulting residue to completely dissolve the insoluble materials to achieve a pH of around pH 8, followed by extraction with chloroform. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain 1-cyclohexyl-7-methoxy-3,4-dihydroisoquinoline (1.87 g).

Workup

  1. temperatureunder heating
  2. temperatureat reflux for 5.5 hours
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. customthe solvent was evaporated
  6. additionAn aqueous 8 M potassium hydroxide solution, water and chloroform were added to the resulting residue
  7. dissolutionto completely dissolve the insoluble materials
  8. extractionfollowed by extraction with chloroform
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was evaporated
  12. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record
ord-3405bd4f47734d88aa64dfb986177f78
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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