Hexamethylenetetramine → HCID 9964644, compound

HRID 1243992Notes

Reaction equation

HRID 1243992 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]([CH3:15])[C:8](=[O:14])[CH:9]3[CH2:13][CH:10]32)=[CH:5][CH:4]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:28](O)=[O:29]>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]([CH3:15])[C:8](=[O:14])[CH:9]3[CH2:13][CH:10]32)=[CH:5][C:4]=1[CH:28]=[O:29]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 21931845HCID 21931845, compound

Product 1

HCID 9964644HCID 9964644, compoundYield 42%

Procedure

To a flame dried round bottom flask equipped with a nitrogen cap was added 972 mg (4.8 mmol) 6-Methoxy-3-methyl-1,1a,3,7b-tetrahydro-3-aza-cyclopropa[a]naphthalen-2-one, 40 ml of trifluoroacetic acid and 806 mg (5.7 mmol) of hexamethylene tetraamine. The mixture was stirred under reflux for 1.5 hours and then cooled to ambient temperature. The reaction mixture was quenched in 200 ml ice and then treated with solid sodium carbonate until pH 9 was reached. The aqueous phase was extracted with chloroform (3×30 ml). The combined organics were then washed with brine followed by drying over sodium sulfate and evaporation in vacuo. The crude residue was taken up in ethyl acetate whereupon crystals formed. Four crops totaling 373 mg were obtained. The mother liquors were purified by silica gel column chromatography eluting with 1/1 ethyl acetate/hexane to afford another 98 mg (total yield 42%) of a white solid which was used directly in the following step. Mass spectrum APCI m/e 232 (p+1).

Workup

  1. customTo a flame dried round bottom flask
  2. customequipped with a nitrogen
  3. customcap
  4. temperatureunder reflux for 1.5 hours
  5. customThe reaction mixture was quenched in 200 ml ice
  6. additiontreated with solid sodium carbonate until pH 9
  7. extractionThe aqueous phase was extracted with chloroform (3×30 ml)
  8. washThe combined organics were then washed with brine
  9. dry with materialby drying over sodium sulfate and evaporation in vacuo
  10. customformed
  11. customwere obtained
  12. customThe mother liquors were purified by silica gel column chromatography
  13. washeluting with 1/1 ethyl acetate/hexane
  14. customto afford another 98 mg (total yield 42%) of a white solid which

Sources & evidence

ORD record
ord-4b7d2fcd4ee14de09547bebf77cae88b
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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