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

HRID 1853451Notes

Reaction equation

HRID 1853451 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 (6 M, 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-ee4f8f0dbb544ec5855142c0d75f3644
Source dataset
uspto-grants-2015_02
Patent number
US08962646B2

Reaction notes

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