HCID 10617412, compound → HCID 10519343, compound

HRID 361830Notes

Reaction equation

HRID 361830 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[C:17]([F:24])[N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pt]=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[C:17]([F:24])[N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10617412HCID 10617412, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10519343HCID 10519343, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

1-Benzyl-4-[N-methyl-N-(3-nitro-6-fluoro-2-pyridinyl)amino]piperidine (EXAMPLE 151, 5.81 g, 16.87 mmol) and platinum oxide (2.5 g) in ethanol (150 ml) is hydrogenated at 10 p.s.i. of hydrogen for one hr. Filtration and removal of the solvent gives 1-benzyl-4-[N-methyl-N-(3-amino-6-fluoro-2-pyridinyl)amino]piperidine. Without further purification, this material is dissolved in 85 ml acetonitrile and cooled to 0°. Acetone (3.76 ml, 51.2 mmol) and fused zinc chloride (465 mg, 3.4 mmol) are added and the mixture refluxed for 8 hrs. It is then poured into water and extracted with chloroform. The extract is dried over sodium sulfate, filtered and concentrated. Chromatography of the concentrate (silica gel, 300 g; ethyl acetate/hexane (50/50)) gives the title compound, NMR (300 MHz, CD3OD) 7.64, 7.36-7.41, 6.73, 3.60, 3.35, 3.00, 2.74, 2.10-2.20, 1.81 and 1.77δ.

Workup

  1. filtrationFiltration and removal of the solvent

Sources & evidence

ORD record
ord-e0dc58d8ea694a58b7f061053ab8b29b
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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