Piperidine → HCID 69005522, compound

HRID 2102409Notes

Reaction equation

HRID 2102409 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5](=O)[CH:6]([Cl:10])[C:7](=O)[CH3:8])[CH3:2].[NH2:13][C:14]1[CH:18]=[CH:17][NH:16][N:15]=1.N1CCCCC1>CC#N.CCO>[CH2:1]([O:3][C:4]([C:5]1[C:6]([Cl:10])=[C:7]([CH3:8])[N:15]2[N:16]=[CH:17][CH:18]=[C:14]2[N:13]=1)=[O:12])[CH3:2]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 3006755ethyl 3-chloro-2,4-dioxopentanoateHCID 178418806HCID 178418806, compound

Product 1

HCID 69005522HCID 69005522, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

3-Chloro-2,4-dioxo-pentanoic ethyl ester (0.325 g, 1.685 mmol) is added to a solution of 3-aminopyrazole (0.14 g, 1.685 mmol) and piperidine (0.18 mL, 1.85 mmol) in MeCN (15 mL), and the reaction mixture heated at 90° C. for 17 hours. After cooling to room temperature, the reaction mixture is diluted with EtOH and concentrated. Purification by flash chromatography (0.5% MeOH in methylene chloride) gives 80 mg (20%) desired product. 1H NMR (400 mHz, CD3OD) δ 8.27 (d, 1H), 6.84 (d, 1H), 4.48 (q, 2H), 2.97 (s, 3H), 1.42 (t, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationconcentrated
  3. customPurification by flash chromatography (0.5% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-c386aaae964f4a1795f2ba01eef0487c
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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