Potassium Cyanide → 6-Butylbenzo[b]quinolizinium perchlorate

HRID 1780915Notes

Reaction equation

HRID 1780915 reaction equation
[C-]#N.[K+].[Br-].[CH:5]1[C:14]2[CH:13]=[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]3=[CH:10][N+:9]=2[CH:8]=[CH:7][CH:6]=1.[Cl:19]([O-:23])(=[O:22])(=[O:21])=[O:20].[Na+]>O.C(O)C.O>[Cl:19]([O-:23])(=[O:22])(=[O:21])=[O:20].[CH2:14]([C:10]1[N+:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:14]=2[CH:13]=[C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=12)[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 202130Benzo(b)quinolizinium, bromide (1:1)HCID 522606Sodium Perchlorate

Product 1

HCID 190474766-Butylbenzo[b]quinolizinium perchlorate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 19096565Water ethanolSolvent

Procedure

A solution of KCN (3g, 0.046 mol) in a minimum of water was added to a solution of benzo[b]quinolizinium bromide (10 g; 0.0385 mol) in 200 ml water. The resulting solid was extracted with an equal volume of methylene chloride. The above organic layer was heated and a solution of bromine (6.4 g) in methylene chloride was added. The resulting yellow solid was isolated, dissolved in ethanol/water, and the resulting solution was treated with sodium perchlorate solution. The perchlorate salt was filtered and recrystallized from ethanol to afford 2 g of 6-cyano-benzo[b]quinolizinium perchlorate (Formula II: R1 =R7 =H; R2 =CN; X- =ClO4-) as a solid.

Workup

  1. extractionThe resulting solid was extracted with an equal volume of methylene chloride
  2. temperatureThe above organic layer was heated
  3. additiona solution of bromine (6.4 g) in methylene chloride was added
  4. customThe resulting yellow solid was isolated
  5. filtrationThe perchlorate salt was filtered
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a996c746ecb54471ac6df38e30d8d3e1
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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