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

HRID 42467Notes

Reaction equation

HRID 42467 reaction equation
CC([N:5]([CH2:9][C:10]1[C:11](=[O:20])[NH:12][C:13]([CH:17]2[CH2:19][CH2:18]2)=[CH:14][C:15]=1[CH3:16])C(=O)[O-])(C)C.CCOC(C)=O.[ClH:27].O1CCOCC1>CO>[ClH:27].[NH2:5][CH2:9][C:10]1[C:11](=[O:20])[NH:12][C:13]([CH:17]2[CH2:18][CH2:19]2)=[CH:14][C:15]=1[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 866773531,1-Dimethylethyl[(6-cyclopropyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)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 4 M 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 (0.22 g, 100% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.78-0.86 (m, 2H), 0.95-1.03 (m, 2H), 1.83 (tt, J=8.46, 5.05 Hz, 1H), 2.16-2.22 (m, 3H), 3.75 (q, J=5.47 Hz, 2H), 5.79 (s, 1H), 8.02 (br. s., 3H), 11.92 (br. s., 1H).

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 (0.22 g, 100% yield)

Sources & evidence

ORD record
ord-da9448aee8874423b88421e823e0b9ce
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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