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

HRID 1808355Notes

Reaction equation

HRID 1808355 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:24]O>>[N:11]1([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12][CH2:13][CH:14]([C:17]([O:19][CH3:24])=[O:18])[CH2:15][CH2:16]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 15125441-Benzyl 4-methyl piperidine-1,4-dicarboxylate

Procedure

1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid (48.5 g) in methanol (485 ml) was cooled to 0° C., and thionyl chloride (13.34 ml) was added dropwise. The mixture was then refluxed for 20 min. (TLC monitoring). When the conversion was complete, the methanol was distilled off and the residue was taken up in water (15 ml) and extracted with ethyl acetate (2×150 ml). The combined organic phases were extracted with water and sat. sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67%)

Workup

  1. temperatureThe mixture was then refluxed for 20 min. (TLC monitoring)
  2. distillationthe methanol was distilled off
  3. extractionextracted with ethyl acetate (2×150 ml)
  4. extractionThe combined organic phases were extracted with water and sat. sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-747a677bd0ba4c70813e7a03b794948f
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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