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

HRID 1603953Notes

Reaction equation

HRID 1603953 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>[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 84541-MethylpyrrolidineSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl isonipecotate (6.0 g, 38.66 mmol), 4-chloropyridine hydrochloride (5.9 g, 38.66 mmol) and N-methylmorpholine (9.3 g mL, 85.00 mmol), were dissolved in N-methylpyrrolidine (50 mL) and the resulting solution was heated at 100° C. for 48 h. The solution was concentrated in vacuo and the residue was dissolved in EtOAc and washed with water and brine (2×100 mL), then dried (Na2SO4) and evaporated. The resulting residue was purified by flash chromatography (5% MeOH/CHC13) to afford 8-1 as a crystalline solid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water and brine (2×100 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe resulting residue was purified by flash chromatography (5% MeOH/CHC13)

Sources & evidence

ORD record
ord-2f75c31df3244d5c90a47d880fcabf74
Source dataset
uspto-grants-1999_11
Patent number
US05990107

Reaction notes

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