Phosphorus oxide (P4O10) → HCID 67537538, compound

HRID 2383034Notes

Reaction equation

HRID 2383034 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][C:11](=O)[CH2:12][CH2:13][CH3:14].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][N:10]=[C:11]2[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 51072902HCID 51072902, compound

Product 1

HCID 67537538HCID 67537538, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

N-[2-(2-methylphenyl)ethyl]butanamide (4.58 g) was dissolved in xylene (30 mL), and then diphosphorus pentoxide (10 g) was added thereto, followed by stirring at 140° C. for 4 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 used to dissolve completely the insoluble materials. The reaction mixture was adjusted to a pH of around 8, and extracted with chloroform. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 5-methyl-1-propyl-3,4-dihydroisoquinoline (2.14 g).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. customthe solvent was evaporated
  4. dissolutionto dissolve completely the insoluble materials
  5. extractionextracted with chloroform
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-84ea8d483bab43bba4106f6cdff8f52e
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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