Ethyl Acetate → HCID 3040670, compound

HRID 1579156Notes

Reaction equation

HRID 1579156 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([S:9][C:10]1[CH:31]=[CH:30][C:13]2[N:14]([CH3:29])[C:15]3[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=3[CH:17]=[C:18]([CH2:19][C:20](=O)[N:21]([CH3:23])[CH3:22])[C:12]=2[CH:11]=1)[CH3:8].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1>[CH2:7]([S:9][C:10]1[CH:31]=[CH:30][C:13]2[N:14]([CH3:29])[C:15]3[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=3[CH:17]=[C:18]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:12]=2[CH:11]=1)[CH3:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 12813991HCID 12813991, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3040670HCID 3040670, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.2 g of lithium aluminum hydride were added in small fractions to a solution of 9 g of 2-ethylthio-5-methyl-11-dimethylcarbamoylmethyl [5H] dibenzo (b,f) azepine in 270 ml of tetrahydrofuran while keeping the temperature below 30°C and the mixture was stirred for 2 hours at room temperature and was cooled to 0°C. Ethyl acetate was added to the mixture followed by a 2N sodium hydroxide solution to dissociate the precipitate formed. The insolubles were removed by filtration and the organic phase was recovered by decanting. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with water, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed over silica gel with a 60-30-10 mixture of cyclohexane-chloroform-triethylamine as eluant which was evaporated to obtain 7.1 g of raw 2-ethylthio-5-methyl-11-(β-dimethylamino ethyl) [5H] dibenzo (b,f) azepine.

Workup

  1. customthe temperature below 30°C
  2. temperaturewas cooled to 0°C
  3. customformed
  4. customThe insolubles were removed by filtration
  5. customthe organic phase was recovered
  6. customby decanting
  7. extractionThe aqueous phase was extracted with ethyl acetate
  8. washthe combined organic phases were washed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated to dryness
  11. customThe residue was chromatographed over silica gel with a 60-30-10 mixture of cyclohexane-chloroform-triethylamine as eluant which
  12. customwas evaporated

Sources & evidence

ORD record
ord-2a0f48aedd1340fe9fc9c5a7ac87ebab
Source dataset
uspto-grants-1976_01
Patent number
US03931151

Reaction notes

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