Triethylamine → HCID 68592895, compound

HRID 1516617Notes

Reaction equation

HRID 1516617 reaction equation
[CH3:1][C:2]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:7][CH2:6][N:5]([C:8](OC(C)(C)C)=O)[CH2:4][CH2:3]1.Cl.ClC1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>Cl.O1CCOCC1>[CH3:1][C:2]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:3][CH2:4][N:5]([C:8]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 162182761-tert-Butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate

Product 1

HCID 68592895HCID 68592895, compound

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

1-tert-Butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate (500 mg, 1.84 mmol) obtained in Step 1 was dissolved in 4N hydrochloric acid/1,4-dioxane (4 ml), and the mixture was stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, and the obtained residue was dissolved in ethanol (18.4 ml). 4-Chloropyridine hydrochloride (276 mg, 1.84 mmol) and triethylamine (2.57 ml, 18.4 mmol) were added thereto, and the reaction mixture was stirred at 170° C. overnight in a sealed tube. The mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate 95:5-10:90) to give the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in ethanol (18.4 ml)
  3. stirringthe reaction mixture was stirred at 170° C. overnight in a sealed tube
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate 95:5-10:90)

Sources & evidence

ORD record
ord-75134912f8524f9c82bc27aac4142295
Source dataset
uspto-grants-2012_07
Patent number
US08227506B2

Reaction notes

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