1,4-Dioxane hydrochloride → (S)-2-Amino-3-(4-amino-phenyl)-N,N-dimethyl-propionamide dihydrochloride

HRID 1872163Notes

Reaction equation

HRID 1872163 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:17](=[O:21])[N:18]([CH3:20])[CH3:19])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)(C)(C)C.[ClH:23].O1CCOCC1>>[ClH:23].[ClH:23].[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)[C:17]([N:18]([CH3:20])[CH3:19])=[O:21]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 20679220(S)-[2-(4-Amino-phenyl)-1-dimethylcarbamoyl-ethyl]-carbamic acid tert-butylester

Product 1

HCID 69688157(S)-2-Amino-3-(4-amino-phenyl)-N,N-dimethyl-propionamide dihydrochloride

Conditions

Temperature
25 °C

Procedure

(S)-[2-(4-Amino-phenyl)-1-dimethylcarbamoyl-ethyl]-carbamic acid tert-butylester (214 mg, 0.7 mmol) was dissolved in 4M HCl-dioxane (2 mL) at 0° C. and the solution stirred for 2 hours at 25° C. The mixture was concentrated and the residue triturated with ether. Yield, 294 mg, 102%; PBMS 208 (MH+, 100%).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue triturated with ether
  3. customYield

Sources & evidence

ORD record
ord-86667107b0d646bda81be457def7be36
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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