Piperidine → HCID 86749038, compound

HRID 2210089Notes

Reaction equation

HRID 2210089 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.N1CCCCC1.[CH:15](=O)/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:18]1([CH:17]=[CH:16][CH:15]=[C:2]2[C:3](=[O:7])[CH2:4][CH2:5][CH2:6][C:1]2=[O:8])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 104341,3-CyclohexanedioneHCID 637511Cinnamaldehyde

Product 1

HCID 86749038HCID 86749038, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 11.2 g (0.1 mol) of 1,3-cyclohexanedione in 110 mL of ethanol was stirred at room temperature while 1 mL of piperidine was added followed by the dropwise addition of 13 mL (0.103 mol) of trans-cinnamaldehyde over a 2 min period. The resulting mixture was stirred at room temperature for 2 hr and then in an ice-bath for 1 hr. The resulting yellow slurry was filtered with suction and the solid dried under high vacuum giving 13.9 g (61.5%) of the title dione. Recrystallization of a sample of this material from ethyl acetate gave yellow solid, mp 115.5°-118° C.

Workup

  1. additionwas added
  2. waitin an ice-bath for 1 hr
  3. filtrationThe resulting yellow slurry was filtered with suction
  4. customthe solid dried under high vacuum
  5. customgiving 13.9 g (61.5%) of the title dione
  6. customRecrystallization of a sample of this material from ethyl acetate
  7. customgave yellow solid, mp 115.5°-118° C.

Sources & evidence

ORD record
ord-8bbe25bb56c5402481f1f90c68e8c36f
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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