Hydrochloric Acid → Hydrochloric Acid

HRID 85544Notes

Reaction equation

HRID 85544 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH2:9][NH:10]C(=O)OC(C)(C)C)=[C:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1.[ClH:25]>>[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[CH:3][C:4]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[ClH:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 679517311,1-Dimethylethyl {[6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinyl]methyl}carbamate

Product 2

HCID 313Hydrochloric AcidYield 86%HCID 674636783-(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinone

Procedure

A solution of 1,1-dimethylethyl {[6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinyl]methyl}carbamate (1.0 g, 3.0 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)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinone as an HCl salt (0.600 g, 86%). LCMS MH+=229.1 1H NMR (400 MHz, DMSO-d6) δ 11.9-12.0 (br s, 1H), 8.03 (br s, 3H), 7.16-7.30 (m, 5H), 5.84 (s, 1H), 3.91 (s, 2H), 3.81 (s, 2H), 2.10 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customdried

Sources & evidence

ORD record
ord-681ab9db10924198bdab84530717f326
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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