HCID 13935138, compound → 9-(((2-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-ol

HRID 580739Notes

Reaction equation

HRID 580739 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[CH:19]([OH:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

4

Reactant 2

HCID 13935138HCID 13935138, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 30256249-(((2-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-olYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

In 100 ml of dry THF was dissolved 4.31 g of 3,4-dihydro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-one and the mechanically stirred solution was cooled to 10° C. under nitrogen. To it was added 5.8 ml of 1M LiAlH4 in THF dropwise over 15 minutes. Within 0.5 hours of addition the reaction was complete by TLC, so it was quenched with 1 ml of saturated ammonium chloride and the salts were filtered. The filtrate was evaporated to a solid which was dissolved in dichloromethane. The dichloromethane solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was refluxed and pentane was added to effect crystallization. The crystals were collected from the cooled mother liquor to yield 3.44 g of solid, mp 158°-160° C.

Workup

  1. additionWithin 0.5 hours of addition the reaction
  2. customwas quenched with 1 ml of saturated ammonium chloride
  3. filtrationthe salts were filtered
  4. customThe filtrate was evaporated to a solid which
  5. dissolutionwas dissolved in dichloromethane
  6. dry with materialThe dichloromethane solution was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. temperatureThe filtrate was refluxed
  9. additionpentane was added to effect crystallization
  10. customThe crystals were collected from the cooled mother liquor

Sources & evidence

ORD record
ord-bf9fd5460b42489e81efb25dd4ba0ad7
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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