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

HRID 1253669Notes

Reaction equation

HRID 1253669 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 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. extractionThe combined organic phases were extracted with water and sat. sodium chloride solution
  4. dry with materialthe extract was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c419bc21f1f549c9b63591eebfe49e25
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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