2-(4-Cyclopentyl-piperazin-1-yl)-isonicotinonitrile → C-[2-(4-Cyclopentyl-piperazin-1-yl)-pyridin-4-yl]-methylamine

HRID 272532Notes

Reaction equation

HRID 272532 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][N:19]=3)[C:15]#[N:16])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.C(OCC)(=O)C.N.[Ni]>[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]([CH2:15][NH2:16])[CH:17]=[CH:18][N:19]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 2

HCID 623696172-(4-Cyclopentyl-piperazin-1-yl)-isonicotinonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 55064210C-[2-(4-Cyclopentyl-piperazin-1-yl)-pyridin-4-yl]-methylamine

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.8 g (11 mmol) 2-(4-cyclopentyl-piperazin-1-yl)-isonicotinonitrile in 10 ml methanol, 15 ml ethyl acetate and 5 ml ammonia was hydrogenated over Raney Nickel with 1 bar hydrogen at 30° C. for 4 h. The mixture was filtered and the residue was washed with 20 ml ethyl acetate three times. After evaporation of the organic phase the residue was purified with preparative HPLC on reversed phase to yield after evaporation of the combined product fractions 1.21 g (42%) of the title compound as yellow solid. (m/e): 261.3 (MH+; 100%).

Workup

  1. filtrationThe mixture was filtered
  2. washthe residue was washed with 20 ml ethyl acetate three times
  3. customAfter evaporation of the organic phase the residue
  4. customwas purified with preparative HPLC on reversed phase
  5. customto yield
  6. customafter evaporation of the combined product fractions 1.21 g (42%) of the title compound as yellow solid

Sources & evidence

ORD record
ord-7b19b3274a124744adffe0dc926ec6d9
Source dataset
uspto-grants-2008_11
Patent number
US07456175B2

Reaction notes

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