Water → HCID 12813968, compound

HRID 1076509Notes

Reaction equation

HRID 1076509 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:22])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:28](OC)=[O:29])([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:10]=2[CH:9]=1.O>O1CCCC1>[Cl:7][C:8]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:22])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:28][OH:29])([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12813961HCID 12813961, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12813968HCID 12813968, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

14 cc of tetrahydrofuran were cooled to 0°C and 0.9 gm of lithium aluminum hydride and then a solution of 1.4 gm of 2-chloro-9-methoxycarbonyl-9-(β-dimethylaminoethyl)-10-methyl-acridane in 14 cc of tetrahydrofuran were added thereto while maintaining the temperature below +10°C. The reaction mixture was then heated at reflux for 21/2 hours and cooled to 0°, +5°C and 10 cc of tetrahydrofuran containing 20% water and then 50 cc of water were added thereto. The reaction mixture was extracted with methylene chloride and filtered. The organic phases were washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to dryness to obtain 1.15 gm of 2-chloro-9-hydroxymethyl-9-(β-dimethylaminoethyl)-10-methyl-acridane which was used as is for the next step.

Workup

  1. temperaturewhile maintaining the temperature below +10°C
  2. temperatureThe reaction mixture was then heated
  3. temperatureat reflux for 21/2 hours
  4. temperaturecooled to 0°, +5°C
  5. extractionThe reaction mixture was extracted with methylene chloride
  6. filtrationfiltered
  7. washThe organic phases were washed with an aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-e9e7a49267924afb8a2596ad561cef4b
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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