Hydrochloric Acid → 3-(aminomethyl)-6-methyl-4-(4-morpholinylmethyl)-2(1H)-pyridinone

HRID 1616854Notes

Reaction equation

HRID 1616854 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[C:4]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:3]=1.Cl.O1CCOCC1>CC(O)=O.[Ni]>[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[CH:3][C:4]=1[CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 674663986-Methyl-4-(morpholinomethyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 674670543-(aminomethyl)-6-methyl-4-(4-morpholinylmethyl)-2(1H)-pyridinoneYield 95.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A clear solution of 6-methyl-4-(4-morpholinylmethyl)-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (0.60 g, 2.57 mmol) in HOAc (20 mL) was treated on an H-Cube apparatus (50 psi, 60° C., 1 mL/min, Raney Nickel cartridge) for 18 hr overnight. LCMS showed that the reaction was complete. The reaction was evaporated to dryness, taken up in a small volume of MeOH and treated with 4 N HCl in dioxane (5 mL, 20.00 mmol). The mixture was evaporated to dryness under vacuum (began to ppt. out during evaporation), triturated with Et2O, filtered and dried under vacuum to give the product 3-(aminomethyl)-6-methyl-4-(4-morpholinylmethyl)-2(1H)-pyridinone (0.76 g, 2.450 mmol, 95% yield) as a light grey solid. 1H NMR (400 MHz, DMSO-d6) δ 6.39 (s, 1H), 4.28 (s, 2H), 3.99 (s, 2H), 3.87 (br. s., 4H), 3.27 (br. s., 4H), 2.22 (s, 3H). MS (ES)+ m/e 238.0 [M+H]+ (weak), 221.3 [M+H]+—NH3 (strong).

Workup

  1. customThe reaction was evaporated to dryness
  2. customThe mixture was evaporated to dryness under vacuum (
  3. customout during evaporation),
  4. customtriturated with Et2O
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ed1f0ddbf6de4958afb72de1ba68f0a8
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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