Piperidine → HCID 69055011, compound

HRID 1727205Notes

Reaction equation

HRID 1727205 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][CH2:11][CH:5]2[C:4](=O)[N:3]=1.P(Cl)(Cl)(Cl)=O.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(O)C>[CH3:1][C:2]1[N:3]=[C:4]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:5]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 24813Phosphorus oxychlorideHCID 69054342HCID 69054342, compound

Product 1

HCID 69055011HCID 69055011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-methyl-7-(phenylmethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(4aH)-one (Preparation 85, 19 g) and phosphorous oxychloride (150 ml) was heated for 1.5 h. The reaction mixture was concentrated and poured onto ice. Sodium carbonate was added to adjust pH to 10, and the product was extracted with chloroform. The organic extracts were concentrated and then purified by passing through a thick pad of florisil (5 cm diameter) the product was eluted with chloroform. Evaporation gave a dark red oil which was dissolved in ethanol (100 ml) and piperidine (25 ml) was added. After 72 h, the reaction mixture was concentrated in vacuo then dissolved in chloroform and basified with sodium hydroxide (2 M solution). The reaction mixture was dried and concentrated before purifying by flash chromatography on florisil eluting the product with petroleum ether (30-40) to give the title compound (12.5 g)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured onto ice
  3. additionSodium carbonate was added
  4. extractionthe product was extracted with chloroform
  5. concentrationThe organic extracts were concentrated
  6. custompurified
  7. washwas eluted with chloroform
  8. customEvaporation
  9. customgave a dark red oil which
  10. concentrationthe reaction mixture was concentrated in vacuo
  11. dissolutionthen dissolved in chloroform
  12. customThe reaction mixture was dried
  13. concentrationconcentrated
  14. custombefore purifying by flash chromatography on florisil eluting the product with petroleum ether (30-40)

Sources & evidence

ORD record
ord-7eaeb237e5084034b0c2462ecf48125c
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

Loading…