1,4-Dioxane hydrochloride → 3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochloride

HRID 2206618Notes

Reaction equation

HRID 2206618 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:10](=[O:17])[NH:11][C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15])(C)(C)C.O1CCOCC1.[ClH:25]>>[ClH:25].[NH2:7][CH2:8][C:9]1[C:10](=[O:17])[NH:11][C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 75466119HCID 75466119, compound

Product 1

HCID 438104513-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochlorideYield 40%

Procedure

tert-butyl((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamate (40 g, 0.27 mol) was added into dioxane/HCl (1 L) and the mixture was stirred at room temperature for 4 hr. The reaction solution was filtrated and concentrated to give crude product. The crude was washed with ethyl acetate (100 mL*2) and EtOH (50 mL*1) and concentrated to give 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride (15 g, 40%). LCMS (M+H+) m/z: calcd. 152.19. found 153.1. 1H NMR (DMSO, 400 MHz) δ 11.84 (s, 1H), 8.07 (s, 3H), 5.96 (s, 1H), 3.76-7.75 (d, J=5.6 Hz, 2H), 2.21 (s, 3H), 2.15 (s, 3H).

Workup

  1. filtrationThe reaction solution was filtrated
  2. concentrationconcentrated
  3. customto give crude product
  4. washThe crude was washed with ethyl acetate (100 mL*2) and EtOH (50 mL*1)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-418085d6e2e74868a3776429c944f334
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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