Triethylamine → 1-(4-Methyl-piperazine-1-carbonyl)-piperidin-4-one hydrochloride

HRID 875146Notes

Reaction equation

HRID 875146 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]([Cl:11])=[O:10])[CH2:5][CH2:4]1.Cl.[OH2:13].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=O.C(N(CC)CC)C>ClCCl>[ClH:11].[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]([N:14]2[CH2:19][CH2:18][C:17](=[O:13])[CH2:16][CH2:15]2)=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochlorideHCID 22021827Piperidone monohydrate hydrochloride

Product 1

HCID 574441601-(4-Methyl-piperazine-1-carbonyl)-piperidin-4-one hydrochlorideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-methylpiperazine-1-carbonyl chloride hydrochloride (19.9 g 0.1 mol) and piperidone monohydrate hydrochloride (15.3 g 0.1 mol), in 200 mL of dichloromethane, dry triethylamine (45 mL, 0.33 mol) was added dropwise. The mixture was stirred for 2 hours. The organic phase was washed with brine (2×20 mL) and dried over sodium sulfate. After filtration, the solvent was evaporated in vacuo and the crude product was dissolved in EtOH (50 mL) and diethylether (100 mL) and treated with HCl 4N in dioxane (25 mL). After 1 hour, the precipitate was filtered and dried in oven to give 13 g (yield 50%) of the title compound.

Workup

  1. washThe organic phase was washed with brine (2×20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated in vacuo
  5. dissolutionthe crude product was dissolved in EtOH (50 mL)
  6. additiondiethylether (100 mL) and treated with HCl 4N in dioxane (25 mL)
  7. waitAfter 1 hour
  8. filtrationthe precipitate was filtered
  9. customdried in oven

Sources & evidence

ORD record
ord-0541a76af06c435f9dfb1590a178b3a4
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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