N-(4-Bromopentyl)phthalimide → HCID 53851053, compound

HRID 1030196Notes

Reaction equation

HRID 1030196 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:24][CH3:25])[C:5]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12].Br[CH:27]([CH3:42])[CH2:28][CH2:29][CH2:30][N:31]1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41]>CCN(CC)CC>[CH3:25][O:24][C:4]1[C:5]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[C:6]2[C:11](=[C:2]([NH:1][CH:27]([CH3:42])[CH2:28][CH2:29][CH2:30][N:31]3[C:35](=[O:36])[C:34]4=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]4[C:32]3=[O:41])[CH:3]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12]

Participants

4

Reactant 2

HCID 240534N-(4-Bromopentyl)phthalimide3×HCID 19822144HCID 19822144, compound

Product 1

HCID 53851053HCID 53851053, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent3×

Procedure

A stirred mixture of 8-amino-6-methoxy-4-methyl-5-[5-(2-thienyl) pentoxy] quinoline (4.00 g, 0.0108 mol) and 4-bromo-1-phthalimidopentane (BPP) (6.40 g, 0.0216 mol) was heated at 110°-115° C. while Et3N (4 ml) was slowly added during 25 min. After 4 h at 115°-120° C., more BPP (6.4 g, 0.0216 mol) and Et3N (2 ml during 10 min) were added and heating was continued for 4 h. A final batch of BPP (1.60 g, 0.0054 mol) and Et3N (1 ml during 5 min) were added and heating was continued for 2 h. On cooling, the mixture was extracted with Et2O (200 ml) leaving behind a gray residue. The extract was washed with H2O (2×75 ml), dried (Na2SO4) and concentrated to a black oil. The oil was dissolved in CHCl3 (12 ml), applied to a silica gel column and eluted with 5% EtOAc in hexane. After recovering the unreacted BPP, the eluting solvent was changed to 10% EtOAc in hexane. Product eluates were combined and concentrated to give 6-methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-[5-(2-thienyl) pentoxy] quinoline as a thick orange-yellow oil, 5.57 g (87%). This material was used without further purification.

Workup

  1. additionwas slowly added during 25 min
  2. temperatureheating
  3. waitwas continued for 4 h
  4. temperatureheating
  5. waitwas continued for 2 h
  6. temperatureOn cooling
  7. extractionthe mixture was extracted with Et2O (200 ml)
  8. customleaving behind a gray residue
  9. washThe extract was washed with H2O (2×75 ml)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated to a black oil
  12. dissolutionThe oil was dissolved in CHCl3 (12 ml)
  13. washeluted with 5% EtOAc in hexane
  14. customAfter recovering the unreacted BPP
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-9c80b658f1744493a7c50f46ac6d926c
Source dataset
uspto-grants-1992_04
Patent number
US05104885

Reaction notes

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