Hexamethylenetetramine → HCID 21931734, compound

HRID 1243987Notes

Reaction equation

HRID 1243987 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][C:6]2([CH3:16])[CH3:15].FC(F)(F)[C:19](O)=[O:20].C1N2CN3CN(C2)CN1C3>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:19]=[O:20])[N:9]([CH3:13])[C:8](=[O:14])[CH2:7][C:6]2([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 21931766HCID 21931766, compound

Product 1

HCID 21931734HCID 21931734, compound

Procedure

To a flame dried round bottom flask equipped with a nitrogen cap was added 83 mg (0.38 mmol) 6-methoxy-1,4,4-trimethyl-3,4-dihydro-1H-quinolin-2-one, 3 ml of trifluoroacetic acid and 53 mg (0.38 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 with 30 ml of saturated aqueous bicarbonate solution and extracted with ethyl acetate (3×30 ml). The combined organics were then washed with brine followed by drying over sodium sulfate and evaporation in vacuo. The crude residue (64 mg; 68%) was used directly in the following step. Mass spectrum APCI m/e 248 (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 with 30 ml of saturated aqueous bicarbonate solution
  6. extractionextracted with ethyl acetate (3×30 ml)
  7. washThe combined organics were then washed with brine
  8. dry with materialby drying over sodium sulfate and evaporation in vacuo

Sources & evidence

ORD record
ord-f3cdd592a46d4ecba3ff40a3cae45ac9
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…