Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-((4,4-diphenylbutyl)amino)-

HRID 580743Notes

Reaction equation

HRID 580743 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:8][CH2:9][CH2:10][NH:11][C:12]2[C:13]3[C:18]([N:19]=[C:20]4[C:25]=2[C:24](=[O:26])[CH2:23][CH2:22][CH2:21]4)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[NH4+]>C1COCC1>[C:27]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][CH2:10][NH:11][C:12]2[C:13]3[C:18]([N:19]=[C:20]4[C:25]=2[CH:24]([OH:26])[CH2:23][CH2:22][CH2:21]4)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 137560583,4-Dihydro-9-(4,4-diphenylbutylamino)acridin-1(2H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 30256311-Acridinol, 1,2,3,4-tetrahydro-9-((4,4-diphenylbutyl)amino)-Yield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 30 ml of dry THF was dissolved 3.00 g of 3,4-dihydro-9-(4,4-diphenylbutyl)aminoacridin-1(2H)-one and the mechanically stirred solution was cooled in an ice bath under nitrogen atmosphere. To the solution under nitrogen was added 6.48 ml of 1M LiAlH4 in THF. Within 0.5 hour after addition the reaction was complete by TLC. The reaction was neutralized with 1 ml of saturated ammonium chloride solution and the inorganics were filtered off. The filtrate was evaporated to an oil and the oil was triturated with 30 ml of 10:1 ether/acetone to yield 2.22 g of solid, mp 147°-148° C. This sample was combined with a 1.0 g sample of an identical previous run and recrystallized from acetone to yield 2.87 g of powder, mp 146°-148° C.

Workup

  1. temperaturethe mechanically stirred solution was cooled in an ice bath under nitrogen atmosphere
  2. additionWithin 0.5 hour after addition the reaction
  3. filtrationthe inorganics were filtered off
  4. customThe filtrate was evaporated to an oil
  5. customthe oil was triturated with 30 ml of 10:1 ether/acetone

Sources & evidence

ORD record
ord-701752ea1c5c4d35a9d02629619c0277
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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