Trifluoromethanesulfonic anhydride → 6-Butylbenzo[b]quinolizinium perchlorate

HRID 742473Notes

Reaction equation

HRID 742473 reaction equation
O[C:2]1([C:14]([CH:15](O)[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:13][CH:12]=[CH:11][CH2:10]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[Cl:36]([O-:40])(=[O:39])(=[O:38])=[O:37].[Na+]>C1C=CC=CC=1>[Cl:36]([O-:40])(=[O:39])(=[O:38])=[O:37].[CH2:16]([C:15]1[N+:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=12)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 522606Sodium PerchlorateHCID 867498052-[1-Hydroxy-6'-(1-hydroxypentyl)-benzyl]pyridine

Product 1

HCID 190474766-Butylbenzo[b]quinolizinium perchlorateYield 11%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a refluxing solution of 11.1 g (0.04 mol) of 2-[1-hydroxy-6'-(1-hydroxypentyl)-benzyl]pyridine in 250 mL of benzene was added 23.9 mL (0.14 mol) of triflic anhydride in 5 min, the mixture was heated for 65 min and then cooled. The reaction mixture was concentrated in vacuo, the residual oil was triturated in ether and decanted. The oil was chromatographed on silica (ethyl acetate/methylene chloride, 1:1 ) to afford an oil, which was treated with sodium perchlorate solution. The salt was triturated in hot water, decanted, and the residue crystallized on cooling. The above solid was crystallized (2×) from ethyl acetate/methylene chloride to afford 1.5 g (11%) of 6-butylbenzo[b]quinolizinium perchlorate (Formula II: R1 =R7 =H; R2 =n-butyl; X- =ClO4-), as a pale solid, m.p. 174°-177° C.

Workup

  1. temperaturethe mixture was heated for 65 min
  2. temperaturecooled
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residual oil was triturated in ether
  5. customdecanted
  6. customThe oil was chromatographed on silica (ethyl acetate/methylene chloride, 1:1 )
  7. customto afford an oil, which
  8. customThe salt was triturated in hot water
  9. customdecanted
  10. customthe residue crystallized
  11. temperatureon cooling
  12. customThe above solid was crystallized (2×) from ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-049a5aa348bd45bf93c824cd8c0d8432
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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