Piperidine → 1-(piperidin-1-yl)butane-1,3-dione

HRID 1055186Notes

Reaction equation

HRID 1055186 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]=[C:8]1[O:12][C:10](=[O:11])[CH2:9]1>C(OC)(C)(C)C>[N:1]1([C:10](=[O:11])[CH2:9][C:8](=[O:12])[CH3:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 12661Diketene

Product 1

HCID 2467741-(piperidin-1-yl)butane-1,3-dioneYield 99.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Conditions

Temperature
-1 °C

Procedure

A solution of 25 g (0.294 mol) piperidin in 100 ml tert.-butyl-methylether was added dropwise to a solution of 26.25 g (0.310 mol) diketene in 200 ml tert.-butyl-methylether at −5 to 0° C. After stirring for 1 hour at −1° C., no starting material was detected anymore by thin-layer chromatography. The reaction mixture was spun off and the residue was distilled under vacuum. 49.55 g of product was obtained as a slightly yellow liquid.

Workup

  1. distillationthe residue was distilled under vacuum

Sources & evidence

ORD record
ord-45d0a5dfe2e34810b1c3dbe202d3e039
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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