Water → HCID 13799022, compound

HRID 280156Notes

Reaction equation

HRID 280156 reaction equation
[N:1]([CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH2:19].[OH-].[Na+]>CCOCC>[NH2:1][CH2:4][CH2:5][CH2:6][O:19][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH2:6][CH2:5][CH:4]2[N:1]1[CH2:11][CH2:12][CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10351958HCID 10351958, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13799022HCID 13799022, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the azido indan ((38 g) (of Step 7 above) in ether (250 ml) is added over a period of 30 min to a suspension of LAH in anhydrous ether (1.5 l) stirred under nitrogen. The mixture is refluxed for about 1.5 hours then cooled and 6 ml H2O added. Aqueous NaOH (15% solution, 6 ml) is added followed by H2O (18 ml) and stirring continued for about 1.5 hours. The reaction mixture is filtered, the solid washed with ether and the filtrate dried over Na2SO4, filtered and concentrated in vacuo. The residue is dissolved in methylene chloride, dried, filtered and evaporated yielding the desired product as an oil.

Workup

  1. temperatureThe mixture is refluxed for about 1.5 hours
  2. temperaturethen cooled
  3. stirringstirring
  4. filtrationThe reaction mixture is filtered
  5. washthe solid washed with ether
  6. dry with materialthe filtrate dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue is dissolved in methylene chloride
  10. customdried
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-12131496f50a477a83d568d7d453794e
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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