Sodium Hydroxide → HCID 23149968, compound

HRID 1670757Notes

Reaction equation

HRID 1670757 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[N:5]([CH3:7])[CH3:6].CCCCCC.C([Li])CCC.C(OC([N:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1)=O)(C)(C)C.[Cl-].[NH4+].[OH-].[Na+]>O1CCCC1>[CH3:6][N:5]([CH3:7])[C:4]1[CH:3]=[C:2]([C:32]2[CH2:33][CH2:34][NH:29][CH2:30][CH:31]=2)[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 1401023-Bromo-N,N-dimethylanilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418244HCID 178418244, compound

Product 1

HCID 23149968HCID 23149968, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Bromo-N,N-dimethylaniline (Aldrich Co., 1.24 g) was dissolved in tetrahydrofuran (18 ml) and the mixture was cooled to −78° C. An n-butyllithium hexane solution (2.6 M, 3.0 ml) was added to the solution and the mixture was stirred for min. 1-(tert-Butoxycarbonyl)-4-piperidone (1.0 g) was added thereto, and the mixture was gradually warmed to room temperature. After completion of the reaction, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with diethyl ether. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate (5:1-2:1)). 10% Aqueous sulfuric acid (5 ml) and 1,4-dioxane (5 ml) were added to the intermediate, and the mixture was stirred with heating at 70° C. for 3 hr. After completion of the reaction, the mixture was cooled to 0° C. A 1N aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to give 4-[3-(dimethylamino)phenyl]-1,2,3,6-tetrahydropyridine (119 mg, yield 10%).

Workup

  1. temperaturethe mixture was gradually warmed to room temperature
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with diethyl ether
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate (5:1-2:1))
  7. addition10% Aqueous sulfuric acid (5 ml) and 1,4-dioxane (5 ml) were added to the intermediate
  8. stirringthe mixture was stirred
  9. temperaturewith heating at 70° C. for 3 hr
  10. customAfter completion of the reaction
  11. temperaturethe mixture was cooled to 0° C
  12. extractionthe mixture was extracted with ethyl acetate
  13. customThe organic layer was dried
  14. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4b62fae47aa743e9a58442859c9a21f3
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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