Hexamethylenetetramine → HCID 21931739, compound

HRID 1243989Notes

Reaction equation

HRID 1243989 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH2:7][CH:6]2[CH3:15].FC(F)(F)[C:18](O)=[O:19].C1N2CN3CN(C2)CN1C3>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:18]=[O:19])[N:9]([CH3:13])[C:8](=[O:14])[CH2:7][CH:6]2[CH3:15]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 21931752HCID 21931752, compound

Product 1

HCID 21931739HCID 21931739, compoundYield 40%

Procedure

To a flame dried round bottom flask equipped with a nitrogen cap was added 110 mg (0.54 mmol) 6-methoxy-1,4-dimethyl-3,4-dihydro-1H-quinolin-2-one, 3 ml of trifluoroacetic acid and 90 mg (0.64 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 first with water and then with 30 ml of saturated aqueous bicarbonate solution and 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, 72 mg, was purified by silica gel column chromatography eluting with 4/6 ethyl acetate/hexane to afford 50 mg (40%) of a yellow solid which was used directly in the following step. Mass spectrum APCI m/e 234 (p+1). Enantiomeric separation was completed on a Chiralpak AD column eluting with 9/1 hexane/ethanol(EtOH) containing 1% diethylamine. The retention times were 12 minutes and 13.8 minutes respectively.

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 first with water
  6. extractionwith 30 ml of saturated aqueous bicarbonate solution and extracted with chloroform (3×30 ml)
  7. washThe combined organics were then washed with brine
  8. dry with materialby drying over sodium sulfate and evaporation in vacuo
  9. customThe crude residue, 72 mg, was purified by silica gel column chromatography
  10. washeluting with 4/6 ethyl acetate/hexane

Sources & evidence

ORD record
ord-717459b9a44a42e7a09f017d6f9afbd5
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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