Ammonia → (3-Piperidin-1-yl-2-pyridinyl)methanamine

HRID 1592488Notes

Reaction equation

HRID 1592488 reaction equation
[N:1]1([C:7]2[C:8]([C:13]#[N:14])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N>CO.[Ni]>[N:1]1([C:7]2[C:8]([CH2:13][NH2:14])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 230165703-Piperidin-1-ylpyridine-2-carbonitrile

Product 1

HCID 67272595(3-Piperidin-1-yl-2-pyridinyl)methanamineYield 63%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-2′-carbonitrile (0.980 g, 5.23 mmol) in MeOH (10 mL) was added to a flask charged with Raney Ni (pre-washed with methanol) (1.0 g) in MeOH (10 mL). After saturated with NH3 gas the mixture was shaken under H2 (40 psi) for 3 h. The reaction mixture was then filtered through a celite cake, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (100:5:1 CH2Cl2/MeOH/NH4OH), affording C-(3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-2′-yl)-methylamine as a pale yellow oil (0.627 g, 63%). 1H NMR (CDCl3) δ 1.53-1.61 (m, 2H), 1.65-1.74 (m, 4H), 2.82 (t, 4H, J=5.4 Hz), 3.99 (s, 2H), 7.11 (dd, 1H, J=4.8, 8.1 Hz), 7.31 (dd, 1H, J=1.5, 8.1 Hz), 8.27 (dd, 1H, J=1.5, 4.8 Hz).

Workup

  1. filtrationThe reaction mixture was then filtered through a celite cake
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on a silica gel column (100:5:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-4ed7896badb34e308b1b29dae01652d9
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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