889851-56-3 → 6-(4-Ethyl-1-piperazinyl)-3-pyridinemethanamine

HRID 490084Notes

Reaction equation

HRID 490084 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[H][H]>[Ni].CO.C(OCC)(=O)C.N>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[N:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

7

Reactant 2

HCID 16748394889851-56-3HCID 178418361HCID 178418361, compound

Product 1

HCID 167882546-(4-Ethyl-1-piperazinyl)-3-pyridinemethanamineYield 103.8%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2 g (8 mmol) 6-(4-ethyl-piperazin-1-yl)-nicotinonitrile, 1.3 g Raney Nickel (B113Z, Degussa) in 25 ml methanol, 15 ml ethyl acetate and 5 ml ammonia aq. (ca. 25%) was treated with 1 bar hydrogen at 30-35° C. for 4 h. The mixture was filtered and the residue washed three times with 20 ml ethyl acetate each and the combined organic phases evaporated to dryness to yield 1.83 g (97%) of the title compound as white crystals. (m/e): 261.1 (MH+; 100%).

Workup

  1. filtrationThe mixture was filtered
  2. washthe residue washed three times with 20 ml ethyl acetate each and the combined organic phases
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-557573b2eabb4b8fa66855591abd3a0c
Source dataset
uspto-grants-2009_05
Patent number
US07528135B2

Reaction notes

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