Sodium hydride → 2-(1-t-Butoxycarbonyl-3-piperidylthio)--3-phenylquinoline

HRID 1903236Notes

Reaction equation

HRID 1903236 reaction equation
[C:1]1([C:7]2[C:8](=[S:17])[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH:31](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH:31]([S:17][C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 132002063-Phenylquinolin-2-thioneHCID 20468243tert-Butyl 3-(tosyloxy)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 539194692-(1-t-Butoxycarbonyl-3-piperidylthio)--3-phenylquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Phenylquinolin-2-thione (5.2 g.) was added to a suspension of sodium hydride (1.15 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (35 ml.) at 0°-5°. When all the hydrogen had evolved, 1-t-butoxycarbonyl-3-p-toluenesulphonyloxypiperidine (7.8 g.) was added and the mixture was heated at 80° for 2 hr. The mixture was cooled to ambient temperature poured into ice-water (350 ml.) and extracted with ethyl acetate (3×150 ml). The ethyl acetate extract was washed with brine (150 ml.) and then dried (MgSO4). The solvent was evaporated to give 2-(1-t-butoxycarbonyl-3-piperidylthio)--3-phenylquinoline, which was used without further purification.

Workup

  1. customat 0°-5°
  2. temperaturethe mixture was heated at 80° for 2 hr
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine (150 ml.)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f5c7ee10f2ab43d6add1fc6c62a6758c
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

Loading…