HCID 12813959, compound → HCID 12813967, compound

HRID 1076502Notes

Reaction equation

HRID 1076502 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]([CH3:25])[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=O>O1CCCC1>[OH:8][CH2:9][C:11]1([CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]([CH3:25])[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

4

Reactant 2

HCID 12813959HCID 12813959, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12813967HCID 12813967, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

20 gm of lithium aluminum hydride were added over 15 minutes to iced 400 cc of tetrahydrofuran and then a solution of 36 gm of 9-methoxycarbonyl-9-(β-dimethylaminoethyl)-10-methyl-acridane in 400 cc of tetrahydrofuran was added thereto over 30 minutes. The mixture was refluxed for 2 hours, then refrigerated and 200 cc of tetrahydrofuran containing 20% water were added thereto at a temperature below 0°C. The mixture was filtered and the filtrate was washed with methylene chloride and distilled to dryness in vacuo. The residue was dissolved in methylene chloride and the organic phase was washed with water, dried over magnesium sulfate and concentrated while adding ethyl acetate to replace the methylene chloride. Crystallization started and after icing for one hour the mixture was filtered. The precipitate was washed with water and was dried to obtain 24.5 gm of 9-hydroxymethyl-9-(β-dimethylaminoethyl)-10-methyl-acridane melting at 150°C. Concentration of the mother liquor gave a second cup of 1.6 gm of the product for a total yield of 79%.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customat a temperature below 0°C
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with methylene chloride
  5. distillationdistilled to dryness in vacuo
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washthe organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. additionwhile adding ethyl acetate
  11. customCrystallization
  12. waitafter icing for one hour
  13. filtrationthe mixture was filtered
  14. washThe precipitate was washed with water
  15. customwas dried

Sources & evidence

ORD record
ord-88075f20376a43468e4cc128d38ec8ee
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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