Ammonia → (3-Morpholinopyridin-2-yl)methanamine

HRID 251055Notes

Reaction equation

HRID 251055 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][O: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][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 672723773-Morpholin-4-yl-pyridine-2-carbonitrile

Product 1

HCID 67271238(3-Morpholinopyridin-2-yl)methanamineYield 94.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 3-morpholin-4-yl-pyridine-2-carbonitrile (0.500 g, 2.64 mmol) in MeOH (10 mL) was added to a flask charged with Raney Ni (pre-washed with methanol) (˜0.5 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 (500:25:6 CH2Cl2/MeOH/NH4OH), affording C-(3-morpholin-4-yl-pyridin-2-yl)-methylamine as a pale yellow oil (0.480 g, 94%). 1H NMR (CDCl3) 2.90-2.93 (m, 4H), 3.85-3.90 (m, 4H), 4.02 (s, 2H), 7.16 (dd, 1H, J=4.5, 8.1 Hz), 7.35 (dd, 1H, J=1.2, 8.1 Hz), 8.33 (dd, 1H, J=1.2, 4.5 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 (500:25:6 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-69e962f166fb4cfe829df6f7bbb16a58
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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