Hydrochloric Acid → 5-(4-(2-aminoethyl)phenyl)pyridin-2(1H)-one hydrochloride

HRID 1482742Notes

Reaction equation

HRID 1482742 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]2[CH:23]=[CH:22][C:11]([CH2:12][CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:10][CH:9]=2)[CH:4]=[CH:3]1.[ClH:24]>>[ClH:24].[NH2:14][CH2:13][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2](=[O:1])[NH:7][CH:6]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 71150146HCID 71150146, compound

Product 1

HCID 711500285-(4-(2-aminoethyl)phenyl)pyridin-2(1H)-one hydrochlorideYield 100%

Procedure

To tert-butyl 4-(6-oxo-1,6-dihydropyridin-3-yl)phenethylcarbamate (10.25 g, 31.0 mmol) was added aqueous hydrochloric acid (6M, 220 mL) and the reaction mixture stirred at reflux overnight. The reaction was cooled to room temperature and the precipitate was filtered, washed with water (5 mL) and dried under reduced pressure (50° C.). The acidic solution was concentrated under reduced pressure and the resultant solid combined with the filtered solid to give 5-(4-(2-aminoethyl)phenyl)pyridin-2(1H)-one hydrochloride (7.80 g, 31.0 mmol, 100% yield).

Workup

  1. temperatureat reflux overnight
  2. filtrationthe precipitate was filtered
  3. washwashed with water (5 mL)
  4. customdried under reduced pressure (50° C.)
  5. concentrationThe acidic solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-781fb23629d1494b92c670ebdc89a94a
Source dataset
uspto-grants-2016_08
Patent number
US09415045B2

Reaction notes

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