10-Acetoxybenzo[b]quinolizinium perchlorate → 6-Butylbenzo[b]quinolizinium perchlorate

HRID 742485Notes

Reaction equation

HRID 742485 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].C(O[C:10]1[C:15]2=[CH:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N+:22]=3[CH:23]=[C:14]2[CH:13]=[CH:12][CH:11]=1)(=O)C>O>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH2:15]([C:23]1[N+:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH:16]=[C:15]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=12)[CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 1

HCID 1047227310-Acetoxybenzo[b]quinolizinium perchlorate

Product 1

HCID 190474766-Butylbenzo[b]quinolizinium perchlorateYield 115.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The above 10-acetoxybenzo[b]quinolizinium perchlorate (3.3 g) was dissolved in 500 mL of water, the solution was boiled, and filtered. To the filtrate was added 100 mL of 30% sodium perchlorate solution and the mixture was chilled. The precipitated solid was isolated by filtration and dried in vacuo to afford 1.9 g of 10-acetoxybenzo[b]quinolizinium perchlorate (Formula II: R1 =R2 =H; R7 =10--OAc; X- =ClO4-). The filtrate was extracted with methylene chloride (3×100 mL), the organic layer was dried and concentrated to yield an additional 0.32 g of the desired acetate perchlorate.

Workup

  1. filtrationfiltered
  2. additionTo the filtrate was added 100 mL of 30% sodium perchlorate solution
  3. temperaturethe mixture was chilled
  4. customThe precipitated solid was isolated by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-92dcc77e8b1e4d81af5a9b70c550239d
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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