Ethyl Acetate → 1-Benzyl-4-[N-methyl-N-(3-nitro-6-chloro-2-pyridinyl)amino]piperidine

HRID 361845Notes

Reaction equation

HRID 361845 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[C:19]([Cl:26])[N:18]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C.O.CCCCCC>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:15])[C:17]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[C:19]([Cl:26])[N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 852392,6-Dichloro-3-nitropyridineHCID 41361281-benzyl-N-methylpiperidin-4-amine

Product 1

HCID 107847861-Benzyl-4-[N-methyl-N-(3-nitro-6-chloro-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

1-Benzyl-4-methylaminopiperidine (EXAMPLE 9, 5.34 g, 25.9 mmol), 2,6-dichloro-3-nitropyridine (5.0 g, 25.9 mmol), and potassium carbonate (4.3 g, 31.1 mmol) in 100 ml acetonitrile are stirred at 20°-25° for 20 hr. The mixture is poured in water and extracted with chloroform. The extract is dried over sodium sulfate, filtered and evaporated to give the crude product. Chromatography (silica gel, 300 g; with 15-25% ethyl acetate in hexane) gives the title compound, NMR (300 MHz, CDCl3) 7.92, 7.19, 6.47, 4.23, 3.40, 2.86, 4.23, 3.40, 2.86, 2.57, 2.02 and 1.69-1.71δ.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract is dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give the crude product

Sources & evidence

ORD record
ord-77da002e19b1470ab196365c6c3b72f1
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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