4-Methylmorpholine → Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate

HRID 618167Notes

Reaction equation

HRID 618167 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.CN1CCOCC1>CN1CCCC1=O>[N:17]1[CH:18]=[CH:19][C:14]([N:1]2[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 70770Ethyl 4-piperidinecarboxylateHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 9899468Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Ethyl isonipecotate (6.0 g, 38.66 mmol), 4-chloropyridine hydrochloride (5.9 g, 38.66 mmol) and N-methylmorpholine (9.3 mL, 85.0 mmol) were dissolved in N-methylpyrrolidinone (50 mL) and the resulting solution heated at 100° for 48 h. The solution was concentrated in vacuo and the residue dissolved in ethyl acetate (200 mL), washed with water and brine (2×100 mL), then dried (Na2SO4) and evaporated. The resulting residue was purified by flash chromatography (5%MeOH/CH2Cl2) to afford 21-1 as a crystalline solid.

Workup

  1. temperaturethe resulting solution heated at 100° for 48 h
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate (200 mL)
  4. washwashed with water and brine (2×100 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe resulting residue was purified by flash chromatography (5%MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-41d35799a15e4e5d869f413c16daae03
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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