Hydrochloric Acid → 3-(Aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one hydrochloride

HRID 873421Notes

Reaction equation

HRID 873421 reaction equation
[NH2:1][CH2:2][C:3]1[C:4](=[O:12])[NH:5][C:6]([CH3:11])=[CH:7][C:8]=1[CH2:9][CH3:10].[ClH:13].O1CCOCC1>C(Cl)Cl>[ClH:13].[NH2:1][CH2:2][C:3]1[C:4](=[O:12])[NH:5][C:6]([CH3:11])=[CH:7][C:8]=1[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 674665833-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one

Product 1

HCID 674665823-(Aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one, (5.6 g, 33 mmol) was suspended in DCM (560 mL) and the insoluble contents/particles were filtered. The filtrate was concentrated and dried. The residue was dissolved in DCM (10 mL) and 4 M HCl in 1,4-dioxane (16 mL, 66 mmol) was added at 0° C. and stirred for 10 min, at which time the reaction mixture was concentrated under high-vacuum and dried. The resulting crude solid was triturated with hexane (150 mL) and filtered. The solid was dried under vacuum. Collected 3-(amino methyl)-4-ethyl-6-methylpyridin-2(1H)-one hydrochloride (5.9 g, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.082-1.120 (t, 3H, J=7.6 Hz), 2.179 (s, 3H), 2.503-2.544 (m, 2H), 3.785-3.798 (d, 2H, J=5.2 Hz), 6.024 (s, 1H), 7.985 (broad s, 2H), 11.858 (broad s, 1H). MS(ES) [M+H]+ 167.2.

Workup

  1. filtrationthe insoluble contents/particles were filtered
  2. concentrationThe filtrate was concentrated
  3. customdried
  4. dissolutionThe residue was dissolved in DCM (10 mL)
  5. concentrationwas concentrated under high-vacuum
  6. customdried
  7. customThe resulting crude solid was triturated with hexane (150 mL)
  8. filtrationfiltered
  9. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-1de38f1075f84bd7ac17c641772c2150
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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