Dibenzylamine → HCID 54033802, compound

HRID 265715Notes

Reaction equation

HRID 265715 reaction equation
FC(F)(F)S(O[C:7]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]([NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[N:8]=1)(=O)=O.[CH2:27]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:23][CH:22]([CH3:24])[CH2:21][NH:20][C:15]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[N:8]=[C:7]([N:34]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:16]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 8471TriethylamineHCID 53725113HCID 53725113, compound

Product 1

HCID 54033802HCID 54033802, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5,7,6,8-tetrahydro-4-[(2-methylpropyl)amino]-3-nitroquinolin-2-yl trifluoromethanesulfonate (4.0 g, 0.01 mole), dibenzylamine (1.9 mL, 0.01 mole), triethylamine (1.4 mL, 0.01 mole) and benzene (100 mL) were combined and heated at reflux for 36 hours. The benzene was evaporated under vacuum and the residue purified by silica gel chromatography eluting with hexane:ethyl acetate 70:30 to provide 4.1 g of the desired product as a viscous orange oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 36 hours
  3. customThe benzene was evaporated under vacuum
  4. customthe residue purified by silica gel chromatography
  5. washeluting with hexane:ethyl acetate 70:30

Sources & evidence

ORD record
ord-1244144a0ddd4d94b2934b61536b5648
Source dataset
uspto-grants-1997_07
Patent number
US05648516

Reaction notes

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