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

HRID 2387930Notes

Reaction equation

HRID 2387930 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 minutes (TLC monitoring). When the reaction was complete, the methanol was distilled off and the residue was taken up in water (15 ml) and with ethyl acetate (2×150 ml). The combined organic phases were extracted with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67%)

Workup

  1. temperatureThe mixture was then refluxed for 20 minutes (TLC monitoring)
  2. distillationthe methanol was distilled off
  3. extractionThe combined organic phases were extracted with water and saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-567cba1211f3430983802869c3e11875
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

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