Hydrochloric Acid → Hydrochloric Acid

HRID 42485Notes

Reaction equation

HRID 42485 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:4](=[O:15])[C:3]=1[CH2:16][NH:17]C(=O)OC(C)(C)C.[ClH:25]>>[NH2:17][CH2:16][C:3]1[C:4](=[O:15])[NH:5][C:6]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:7][C:2]=1[CH3:1].[ClH:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 679517321,1-Dimethylethyl {[4-methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinyl]methyl}carbamate

Product 2

HCID 313Hydrochloric AcidYield 87%HCID 674681903-(aminomethyl)-6-benzyl-4-methylpyridin-2(1H)-one

Procedure

A solution of 1,1-dimethylethyl {[4-methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinyl]methyl}carbamate (1.2 g, 3.66 mmol) in 4N HCl (in 15 mL 1,4 dioxane) was heated to 60° C. for 1 h. The mixture was cooled to room temperature. The mixture was filtered and dried to give 3-(aminomethyl)-4-methyl-6-(phenylmethyl)-2(1H)-pyridinone as an HCl salt (0.725 g, 87%). LCMS MH+=229.1 1H NMR (400 MHz, DMSO-d6) δ 11.9-12.0 (br s, 1H), 7.99 (br s, 3H), 7.20 (s, 5H), 5.97 (s, 1H), 3.72-3.75 (m, 4H), 2.17 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customdried

Sources & evidence

ORD record
ord-3428dbeafa084f7ca01a7a89cdbe1c78
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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