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

HRID 873440Notes

Reaction equation

HRID 873440 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, 1 H), 4.28 (s, 2 H), 3.99 (s, 2 H), 3.87 (br. s., 4 H), 3.27 (br. s., 4 H), 2.22 (s, 3 H). 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-54f61752458346dca34fe8bc53fd1e45
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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