Triethylamine → 1-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-one

HRID 383860Notes

Reaction equation

HRID 383860 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.CCN(CC)CC.Cl[C:17]1[S:21][N:20]=[C:19]([CH3:22])[N:18]=1>CCO>[CH3:22][C:19]1[N:18]=[C:17]([N:2]2[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]2)[S:21][N:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30848514-Piperidone hydrochlorideHCID 129191595-Chloro-3-methyl-1,2,4-thiadiazole

Product 1

HCID 592585101-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-oneYield 8.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of piperidin-4-one HCl salt (4.08 g, 30 mmol) and Et3N (20 mL, 78.6 mmol) in EtOH (50 mL) was added 5-chloro-3-methyl-1,2,4-thiadiazole (4.05 g, 30 mmol). The mixture was heated to reflux for 1.5 hours and then concentrated to dryness. The residue was dissolved in EtOAc. The solution was washed with water (30 mL×3) and brine (30 mL), dried over Na2SO4, and concentrated to dryness. The residue was recrystalled from ether to give 1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-one (510 mg, 8.6%). 1H-NMR (300 MHz, CDCl3) δ 3.86 (t, J=6.3 Hz, 4H), 2.62 (t, J=6.3, Hz, 4H), 2.44 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in EtOAc
  5. washThe solution was washed with water (30 mL×3) and brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-18d533abb515450a9f8b6b2dce905825
Source dataset
uspto-grants-2013_02
Patent number
US08367691B2

Reaction notes

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