(2,6-Dimethylpiperidin-1-yl)acetonitrile → 2,6-Dimethyl-1-piperidineethanamine

HRID 1669200Notes

Reaction equation

HRID 1669200 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[N:3]1[CH2:9][C:10]#[N:11]>[Ni].CCO>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[N:3]1[CH2:9][CH2:10][NH2:11]

Participants

4

Reactant 1

HCID 12765385(2,6-Dimethylpiperidin-1-yl)acetonitrile

Product 1

HCID 31492662,6-Dimethyl-1-piperidineethanamineYield 78.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of nitrile 279 (3.13 g, 20.6 mmol) and Raney Nickel (50% w/w suspension in water, ca. 2 mL) in EtOH (30 mL) and cNH3 (2 mL) was stirred under H2 (60 psi) for 5 h. The suspension was filtered through Celite, washed with EtOH (3×10 mL) and the solvent evaporated to give diamine 280 (2.52 g, 78%) as a colourless oil which was used without further purification: 1H NMR δ 2.71-2.76 (m, 2H, CH2N), 2.63-2.68 (m, 2H, CH2N), 2.41-2.47 (m, 2H, 2×CH), 1.49-1.55 (m, 2H, CH2), 1.43 (br s, 2H, NH2), 1.25-1.42 (m, 4H, 2×CH2), 1.11 (d, J=6.3 Hz, 6H, 2×CH3); MS m/z 157 (MH+, 100%).

Workup

  1. filtrationThe suspension was filtered through Celite
  2. washwashed with EtOH (3×10 mL)
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-7736bb1f872347ec9ccf6fae749f3fbf
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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