Ethanol → Ethyl 6-oxopiperidine-3-carboxylate

HRID 741868Notes

Reaction equation

HRID 741868 reaction equation
[C:1]([CH:4]1[CH2:9][NH:8][C:7](=[O:10])[CH2:6][CH2:5]1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH2:15](O)[CH3:16]>>[CH2:15]([O:2][C:1]([CH:4]1[CH2:9][NH:8][C:7](=[O:10])[CH2:6][CH2:5]1)=[O:3])[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 5600906-Oxopiperidine-3-carboxylic acid

Product 1

HCID 15386078Ethyl 6-oxopiperidine-3-carboxylate

Procedure

To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3H), 1.78-1.92 (m, 1 H), 1.95-2.08 (m, 1H), 2.15-2.31 (m, 2H), 2.78-2.89 (m, 1H), 3.25-3.40 (m, 2H), 4.12 (t, J=7 Hz, 2H), 7.95 (s, 1H).

Workup

  1. customThe resulting solution was evaporated to dryness
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-d05c65c5b6cd4d9bb78e429beffcc27a
Source dataset
uspto-grants-1996_09
Patent number
US05552545

Reaction notes

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