Trifluoromethanesulfonic anhydride → 6-Butylbenzo[b]quinolizinium perchlorate

HRID 1780898노트

반응식

HRID 1780898 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 190474766-Butylbenzo[b]quinolizinium perchlorate수율 11%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6f930ecb5bb04d1aa44f812c6ea43e74
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05631264

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