4-Methylmorpholine → 1-Benzyl 4-methyl piperidine-1,4-dicarboxylate

HRID 215941Notes

Reaction equation

HRID 215941 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1.CN1CCOCC1>C(#N)C.C([O-])(O)=O.[Na+]>[N:12]1([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 10387Benzyl chloroformateHCID 424914Methyl isonipecotate

Product 1

HCID 15125441-Benzyl 4-methyl piperidine-1,4-dicarboxylateYield 62%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Benzyl chloroformate (11.0 mL, 0.0768 mol) was added into a solution of methyl piperidine-4-carboxylate (10.0 g, 0.0698 mol) and 4-methylmorpholine (15.4 mL, 0.140 mol) in acetonitrile (20.0 mL). After 30 min, the mixture was diluted with NaHCO3 (7.5%), extracted with ethyl acetate (AcOEt) (3×30 mL). The combined organic layers were dried over Na2SO4, filtered, concentrated to afford 1-benzyl 4-methyl piperidine-1,4-dicarboxylate (12 gram) which was directly used in next step without further purification.

Workup

  1. extractionextracted with ethyl acetate (AcOEt) (3×30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-02ae635f1f5240828e4491962cdf2806
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

Loading…