Sodium Hydroxide → HCID 22247339, compound

HRID 1107975Notes

Reaction equation

HRID 1107975 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[C:9]([CH3:18])[C:10]([CH2:15][C:16]#[N:17])=[C:11]([CH3:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].[OH-:19].[Na+]>C(O)C.O>[CH2:1]([N:4]1[C:13]2[C:8](=[C:9]([CH3:18])[C:10]([CH2:15][C:16](=[O:19])[NH2:17])=[C:11]([CH3:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH2:2][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22247314HCID 22247314, compound

Product 1

HCID 22247339HCID 22247339, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1-Acetyl-6-cyanomethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline (2.7 g) was dissolved in ethanol (30 ml), and a solution of NaOH (4.4 g) in water (10 ml) was added, which was followed by refluxing for 10 hr under nitrogen. The solvent was evaporated under reduced pressure, and the residue was extracted with chloroform (100 ml). After washing with water, the chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained 6-carbamoylmethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline was dissolved in N,N-dimethylformamide (10 ml), and octyl bromide (1.6 g), potassium carbonate (1.2 g) and potassium iodide (166 mg) were added, which was followed by stirring at 40° C. for 10 hr in nitrogen. The reaction mixture was extracted with ethyl acetate (100 ml). After washing with water, the ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1-10/1) to give 600 mg of 1-octyl-6-carbamoylmethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline as crystals.

Workup

  1. temperatureby refluxing for 10 hr under nitrogen
  2. customThe solvent was evaporated under reduced pressure
  3. extractionthe residue was extracted with chloroform (100 ml)
  4. washAfter washing with water
  5. dry with materialthe chloroform layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionThe obtained 6-carbamoylmethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline was dissolved in N,N-dimethylformamide (10 ml)
  8. additionoctyl bromide (1.6 g), potassium carbonate (1.2 g) and potassium iodide (166 mg) were added
  9. extractionThe reaction mixture was extracted with ethyl acetate (100 ml)
  10. washAfter washing with water
  11. dry with materialthe ethyl acetate layer was dried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1-10/1)

Sources & evidence

ORD record
ord-1a48e39896944d2185f726f58c44052e
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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