HCID 20150321, compound → HCID 20150294, compound

HRID 568342Notes

Reaction equation

HRID 568342 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[C:18]([O:20][CH2:21][C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>CO.Cl.C(O)(C)C.C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:19]=[C:18]([O:20][CH2:21][C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 1

HCID 20150321HCID 20150321, compound

Product 1

HCID 20150294HCID 20150294, compoundYield 28.9%

Reagents, catalysts & solvents 4

HCID 297MethaneCatalystHCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

4-{[2-(4-Nitrophenyl)-4-quinolyl]oxyacetyl}morpholine (3.93 g), prepared according to Example 31, dissolved in methanol (80 cc) is hydrogenated at 40° C. for 30 minutes and then at room temperature (approximately 20° C.) and under atmospheric pressure in the presence of a 5N solution (4 cc) of hydrochloric acid in isopropanol and palladinized charcoal (10% Pd) (0.4 g) as catalyst. After absorption of the theoretical amount of hydrogen, normal sodium hydroxide solution (25 cc) is added to the reaction mixture in order to redissolve the precipitate formed. After filtration, the solvent is removed under reduced pressure and the residual aqueous phase is taken up with methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue (2.9 g) is dissolved in hot ethyl acetate (15 cc); ethyl ether (30 cc) is then added, and the precipitate is filtered off and chromatographed on silica gel using a toluene/methanol/diethylamine (90:5:5 by volume) mixture. 4-{[2-(4-Aminophenyl)-4-quinolyl]oxyacetyl}morpholine (1.05 g), m.p. 174° C., is thereby isolated.

Workup

  1. customat room temperature
  2. custom(approximately 20° C.)
  3. customAfter absorption of the theoretical amount of hydrogen, normal sodium hydroxide solution (25 cc)
  4. additionis added to the reaction mixture in order
  5. dissolutionto redissolve the precipitate
  6. customformed
  7. filtrationAfter filtration
  8. customthe solvent is removed under reduced pressure
  9. washThe organic phase is washed with water
  10. dry with materialdried over magnesium sulphate
  11. customevaporated under reduced pressure
  12. dissolutionThe residue (2.9 g) is dissolved in hot ethyl acetate (15 cc)
  13. additionethyl ether (30 cc) is then added
  14. filtrationthe precipitate is filtered off
  15. customchromatographed on silica gel using a toluene/methanol/diethylamine (90:5:5 by volume) mixture

Sources & evidence

ORD record
ord-f0a729c8012e43d5a2a3c05964fd2e3c
Source dataset
uspto-grants-1988_03
Patent number
US04728647

Reaction notes

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