HCID 67576728, compound → HCID 10762096, compound

HRID 361809Notes

Reaction equation

HRID 361809 reaction equation
[CH3:1][C:2]([CH3:27])([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]([CH3:26])[C:14]2[C:19]([NH:20][C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3]>C(O)C.[Ni]>[CH3:27][C:2]([CH3:3])([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]([CH3:26])[C:14]2[C:19]([NH:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH3:23])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:1]

Participants

4

Reactant 1

HCID 67576728HCID 67576728, compound

Product 1

HCID 10762096HCID 10762096, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[N-methyl-N-(3-(1,1-dimethylprop-2-enylamino)-2-pyridinyl)amino]piperidine (EXAMPLE 62, 2.41 g) in absolute ethanol (40 ml) under nitrogen is added wet Raney Nickel (620 mg). The mixture is put under a hydrogen atmosphere at 40 psi for 21 hrs, filtered through diatomaceous earth, and concentrated to give an oil which is chromatographed (silica gel, 70-230 mesh, 250 g; eluting with a gradient of ethyl acetate/hexane (10/90-35/65)), to give the title compound, NMR (CDCl3) 7.67, 7.04, 6.87, 4.87, 4.04, 3.20, 2.76, 2.61, 1.71, 1.50, 1.45, 1.31 and 0.86δ.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated
  3. customto give an oil which
  4. customis chromatographed (silica gel, 70-230 mesh, 250 g
  5. washeluting with a gradient of ethyl acetate/hexane (10/90-35/65)),

Sources & evidence

ORD record
ord-e393eafd3bd94cfe905b1715fb1ee02b
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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