HCID 796577, compound → Dofequidar

HRID 1647705Notes

Reaction equation

HRID 1647705 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2.[C:16]1([CH:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:31]1([CH:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:23]([N:25]2[CH2:26][CH2:27][N:28]([CH2:15][CH:2]([OH:1])[CH2:3][O:4][C:5]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:6]=3[CH:7]=[CH:8][CH:9]=[N:10]4)[CH2:29][CH2:30]2)=[O:24])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 796577HCID 796577, compoundHCID 112178995-(Oxiran-2-ylmethoxy)quinoline

Product 1

HCID 213040DofequidarYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

71 g of the above-mentioned 5-(2,3-epoxypropoxy) quinoline and 94 g of N-(2,2-diphenylacetyl)piperazine were dissolved in 1.5 l of ethanol and then the resulting solution was refluxed with heating for 3 hours. After the reaction, ethanol was evaporated and the residue was purified by chromatography. The elution was carried out with a solvent miture of chloroform:methanol=50:1 (volume ratio) and the targeted fraction was concentrated under reduced pressure to obtain 101 g of 5-[3-{4-(2,2diphenylacetyl)piperazin-1-yl}-2- hydroxypropoxy]quinoline (compound No. 1).

Workup

  1. temperaturethe resulting solution was refluxed
  2. temperaturewith heating for 3 hours
  3. customwas evaporated
  4. customthe residue was purified by chromatography
  5. washThe elution
  6. concentrationmethanol=50:1 (volume ratio) and the targeted fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9aa279b38c2c468a96154541f6d394e4
Source dataset
uspto-grants-1995_07
Patent number
US05434155

Reaction notes

Loading…