HCID 54438806, compound → HCID 20468223, compound

HRID 1903237Notes

Reaction equation

HRID 1903237 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([S:14][C:15]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:9]1)=O)CCC>C(OCC)(=O)C>[C:25]1([C:24]2[C:15]([S:14][CH:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[N:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 54438806HCID 54438806, compound

Product 1

HCID 20468223HCID 20468223, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(1-Butoxycarbonyl-3-piperidylthio)--3-phenylquinoline (4.2 g.) was added to 6 M-hydrogen chloride in ethyl acetate (50 ml.), and the mixture was stirred at ambient temperature for 1 hr. The solvent was evaporated and the residual oil was dissolved in diethyl ether (100 ml.) and extracted with 1 M-hydrochloric acid solution (20×30 ml.). The hydrochloric acid extract was adjusted to pH 10 with saturated sodium carbonate solution and extracted with diethyl ether (2×100 ml.). The diethyl ether extract was washed with brine (75 ml.) and then dried (MgSO4). The solvent was evaporated to give 3-phenyl-2-(3-piperidylthio)quinoline which was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residual oil was dissolved in diethyl ether (100 ml.)
  3. extractionextracted with 1 M-hydrochloric acid solution (20×30 ml.)
  4. extractionThe hydrochloric acid extract
  5. extractionextracted with diethyl ether (2×100 ml.)
  6. extractionThe diethyl ether extract
  7. washwas washed with brine (75 ml.)
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-90563d7b62804599b0b8e2f11ad605fd
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

Loading…