Piperidine → HCID 21560000, compound

HRID 1578386Notes

Reaction equation

HRID 1578386 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:8][CH2:9][C:10]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:12])=[O:7])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1013593-(4-Fluorobenzoyl)propionic acid

Product 1

HCID 21560000HCID 21560000, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15 g of β-p-fluorobenzoyl-propionic acid and 8.0 g of triethylamine in 100 ml of tetrahydrofuran, was gradually added 8.3 g of ethyl chlorocarbonate while the reaction mixture was kept below 0°C. After being stirred for 25 minutes at a temperature below 0°C, the mixture was added with 6.5 g of piperidine and stirred for another 2 hours. Then the precipitate formed was filtered off and the filtrate was concentrated to dryness under reduced pressure. The residue was recrystallized from hexane to obtain 11 g of 1-(β-p-fluorobenzoylpropionyl)piperidine, melting at 70° - 71°C.

Workup

  1. customwas kept below 0°C
  2. stirringstirred for another 2 hours
  3. customThen the precipitate formed
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated to dryness under reduced pressure
  6. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-50b3ab3eda6947fa85c5a0ff9d4f4c74
Source dataset
uspto-grants-1976_02
Patent number
US03936468

Reaction notes

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