Phosphorus oxide (P4O10) → HCID 50994820, compound

HRID 404983Notes

Reaction equation

HRID 404983 reaction equation
[CH:1]1([N:6]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[C:7](=O)[O:8]C)[CH2:5][CH2:4][CH2:3][CH2:2]1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[CH:1]1([N:6]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[C:7]2=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 50994819HCID 50994819, compound

Product 1

HCID 50994820HCID 50994820, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To a solution of methyl cyclopentyl(3-methoxyphenethyl)carbamate (1.39 g, 5 mmol) in POCl3 (20 mL) was added P2O5 (1.4 g, 10 mmol). The reaction mixture was heated at reflux for 2 h. Excess POCl3 was removed under reduced pressure and the residue was quenched with ice water. The mixture was neutralized with Na2CO3 and extracted with ethyl acetate. The organic phase was dried over Na2SO4. Removal of the solvent in vacuo followed by chromato-graphic purification afforded 2-cyclopentyl-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one 1H NMR (400 MHz, CDCl3): δ 8.00 (d, 1H, J=8.6 Hz), 6.81 (d, 1H, J=8.6 Hz), 6.63 (s, 1H), 5.18-5.14 (m, 1H), 3.85 (t, 1H, J=6.7 Hz), 2.88 (t, 1H, J=6.7 Hz), 1.88-1.70 (m, 2H), 1.64-1.63 (m, 4H), 1.62-1.61 (m, 2H). LC-MS (ESI) Calcd for C15H19NO2 [M+H]+: 246.14. Found: 246.00.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. customExcess POCl3 was removed under reduced pressure
  4. customthe residue was quenched with ice water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customRemoval of the solvent in vacuo
  8. customfollowed by chromato-graphic purification

Sources & evidence

ORD record
ord-52ca22004a9d45cebdb2e6ec58e300ca
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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