Sodium → 1,2,3,4,5,6-Hexahydro-8-methoxy-1,3-dimethyl-2,6-methano-1,3-benzodiazocine

HRID 258081Notes

Reaction equation

HRID 258081 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][CH3:18].[Na]>C(O)CCC>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[N:9]([CH3:13])[CH:8]3[CH2:7][CH:6]([CH2:15][CH2:16][N:17]3[CH3:18])[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 5360545Sodium2×HCID 15678873HCID 15678873, compound

Product 1

HCID 98375521,2,3,4,5,6-Hexahydro-8-methoxy-1,3-dimethyl-2,6-methano-1,3-benzodiazocineYield 52.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a stirred solution of 4.50 g of 3,4-dihydro-6-methoxy-1-methyl-4-[2-(methylamino)ethyl]-2(1H)-quinolinone in 450 ml of refluxing n-butanol was added, incrementally over a period of 1.5 hours, 27.0 g of sodium. The resulting mixture was stirred at reflux until all of the sodium was consumed, and then it was cooled, and diluted with water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic layers were washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The concentrate was purified by means of column chromatography on silica gel (elution with triethylamine/methanol/ethyl acetate) followed by recrystallization from diethyl ether-pentane to afford 2.20 g (52%) of 1,2,3,4,5,6-hexahydro-8-methoxy-1,3-dimethyl-2,6-methano-1,3-benzodiazocine, m.p. 72°-73.5° C.

Workup

  1. customwas consumed
  2. temperatureit was cooled
  3. additiondiluted with water
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride, dried over 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)
  11. customfollowed by recrystallization from diethyl ether-pentane

Sources & evidence

ORD record
ord-0276427df997404f82d47e60af5f2a8b
Source dataset
uspto-grants-1993_11
Patent number
US05264575

Reaction notes

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