Sodium → HCID 19782493, compound

HRID 258082Notes

Reaction equation

HRID 258082 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)[CH2:7][CH:6]2[CH2:15][CH2:16][NH:17]C(C1C=CC=CC=1)C.[Na]>C(O)CCC>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[N:9]([CH3:13])[C:8]3([CH:6]([C:5]4[CH:10]=[CH:11][CH:12]=[CH:3][CH:4]=4)[CH3:7])[CH2:7][CH:6]([CH2:15][CH2:16][NH:17]3)[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 5360545Sodium2×HCID 15678875HCID 15678875, compound

Product 1

HCID 19782493HCID 19782493, compoundYield 117.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a stirred solution of 3.65 g of 3,4-dihydro-6-methoxy-1-methyl-4-[2-[(1-phenylethyl)amino]ethyl]-2(1H)-quinolinone in 270 ml of refluxing n-butanol was added, incrementally over a period of 1.5 hours, 7.40 g of sodium. The resulting mixture was stirred at reflux until all of the sodium was consumed, and then was cooled, and diluted with water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phase was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The concentrate was purified by means of column chromatography on silica gel (elution with triethylamine/methanol/ethyl acetate) to afford 2.04 g (59%) of 1,2,3,4,5,6-hexahydro-8-methoxy-1-methyl-2-(1-phenylethyl)-2,6-methano-1,3-benzodiazocine as an oil.

Workup

  1. customwas consumed
  2. temperaturewas cooled
  3. additiondiluted with water
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate
  6. washThe combined organic phase was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was purified by means of column chromatography on silica gel (elution with triethylamine/methanol/ethyl acetate)

Sources & evidence

ORD record
ord-61aedc3426434f6fa5c65ca56df4c21d
Source dataset
uspto-grants-1993_11
Patent number
US05264575

Reaction notes

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