Hydrochloric Acid → 3-(Aminomethyl)-6-cyclopropyl-4-methyl-2(1H)-pyridinone hydrochloride

HRID 1522342Notes

Reaction equation

HRID 1522342 reaction equation
[CH:1]1([C:4]2[NH:9][C:8](=[O:10])[C:7]([CH2:11][NH:12]C(=O)OC(C)(C)C)=[C:6]([CH3:20])[CH:5]=2)[CH2:3][CH2:2]1.CCOC(C)=O.[ClH:27].O1CCOCC1>CO>[ClH:27].[NH2:12][CH2:11][C:7]1[C:8](=[O:10])[NH:9][C:4]([CH:1]2[CH2:2][CH2:3]2)=[CH:5][C:6]=1[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 67951704Tert-butyl ((6-cyclopropyl-4-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamate

Product 1

HCID 671241643-(Aminomethyl)-6-cyclopropyl-4-methyl-2(1H)-pyridinone hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl [(6-cyclopropyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate (0.28 g, 1.006 mmol) was added to EtOAc (9 mL) and methanol (1.0 mL). The suspension was stirred at room temperature for 5 min., followed by addition of 4M HCl in dioxane (5.03 mL, 20.12 mmol), and the contents were stirred at room temperature overnight. The volatiles were then removed in vacuo to afford a solid. The solid was triturated with ether, filtered, and dried in a vacuum oven at 45° C. for 4 h. The title compound was collected as 0.22 g (100% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.78-0.86 (m, 2 H), 0.95-1.03 (m, 2 H), 1.83 (tt, J=8.46, 5.05 Hz, 1 H), 2.16-2.22 (m, 3 H), 3.75 (q, J=5.47 Hz, 2 H), 5.79 (s, 1 H), 8.02 (br. s., 3 H), 11.92 (br. s., 1 H).

Workup

  1. stirringthe contents were stirred at room temperature overnight
  2. customThe volatiles were then removed in vacuo
  3. customto afford a solid
  4. customThe solid was triturated with ether
  5. filtrationfiltered
  6. customdried in a vacuum oven at 45° C. for 4 h
  7. customThe title compound was collected as 0.22 g (100% yield)

Sources & evidence

ORD record
ord-fd14602be2a04032b037feea24e6466d
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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