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

HRID 641184Notes

Reaction equation

HRID 641184 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 (C3) (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 h 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 recrystallized from ether to give 1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-one (D1) (510 mg). 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 h
  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
  8. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-793571c76f1e4385a26b64a8c6545c4a
Source dataset
uspto-grants-2010_04
Patent number
US07696201B2

Reaction notes

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