2,4,6-Trifluorobenzoyl chloride → Benzamide, 2,4,6-trifluoro-N-(6-((1-methyl-4-piperidinyl)carbonyl)-2-pyridinyl)-, hydrochloride (1:1)

HRID 404228

Reaction equation

HRID 404228 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1.[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[C:19]=1[C:20]([Cl:22])=[O:21]>O1CCOCC1>[ClH:22].[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[C:19]=1[C:20]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1)=[O:21]

Participants

4

Reactant 2

HCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 11401723(6-Aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone

Product 1

HCID 17980336Benzamide, 2,4,6-trifluoro-N-(6-((1-methyl-4-piperidinyl)carbonyl)-2-pyridinyl)-, hydrochloride (1:1)Yield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine 2-amino-6-(1-methylpiperidin-4-ylcarbonyl)pyridine (0.20 g, 0.92 mmol), 2,4,6-Trifluorobenzoyl chloride (0.357 g, 1.84 mmol), and 1,4-Dioxane (10 mL), and stir while heating at reflux. After 3 hr., cool the reaction mixture to ambient temperature and concentrate. Load the concentrated mixture onto an SCX column (10 g), wash with methanol, and elute with 2M ammonia in methanol. Concentrate the eluent to obtain the free base of the title compound as an oil (0.365 g (>100%)). Dissolve the oil in methanol (5 mL) and treat with ammonium chloride (0.05 g, 0.92 mmol). Concentrate the mixture and dry under vacuum to obtain the title compound. HRMS Obs. m/z 378.1435, Calc. m/z 378.1429; m.p. 255° C. (dec).

Workup

  1. temperaturewhile heating
  2. temperatureat reflux
  3. concentrationconcentrate
  4. washLoad the concentrated mixture onto an SCX column (10 g), wash with methanol
  5. washelute with 2M ammonia in methanol
  6. concentrationConcentrate the eluent

Sources & evidence

ORD record
ord-2a6312686e8842c5881fe80d6a74becd
Source dataset
uspto-grants-2014_06
Patent number
US08748459B2

Linked notes

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