Trifluoromethanesulfonic anhydride → 6-Butylbenzo[b]quinolizinium perchlorate

HRID 1780898ノート

反応式

HRID 1780898 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 190474766-Butylbenzo[b]quinolizinium perchlorate収率 11%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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 (2x) 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.

後処理

  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 (2x) from ethyl acetate/methylene chloride

出典と根拠

ORDレコード
ord-6f930ecb5bb04d1aa44f812c6ea43e74
出典データセット
uspto-grants-1997_05
特許番号
US05631264

反応ノート

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