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

HRID 1517367Notes

Reaction equation

HRID 1517367 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 control). When the reaction was complete, the methanol was distilled off, 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 and the extract was dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67%)

Workup

  1. temperatureThe mixture was then refluxed for 20 min (TLC control)
  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 materialthe extract was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-007faffd1ba1440e823aaa754b6a4b78
Source dataset
uspto-grants-2012_07
Patent number
US08232288B2

Reaction notes

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