ChemicalBook CAS DataBase List MORPHOLIN-4-YL-PHENYL-ACETIC ACID HYDROCHLORIDE

MORPHOLIN-4-YL-PHENYL-ACETIC ACID HYDROCHLORIDE synthesis

5synthesis methods

Product Name:MORPHOLIN-4-YL-PHENYL-ACETIC ACID HYDROCHLORIDE
CAS Number:91641-50-8
Molecular formula:C12H16ClNO3
Molecular Weight:257.7133

22083-23-4

MORPHOLIN-4-YL-PHENYL-ACETIC ACID HYDROCHLORIDE

91641-50-8

Preparation of 2-morpholino-2-phenylacetic acid hydrochloride (I39): ethyl 2-morpholino-2-phenylacetate (0.34 g, 1.36 mmol) was dissolved in dioxane (11.4 mL) and 37% hydrochloric acid (1.1 mL, 13.6 mmol) was added slowly and dropwise. The reaction mixture was stirred under reflux conditions overnight. 37% hydrochloric acid (1.1 mL, 13.6 mmol) was added again and the reaction was continued at reflux for 24 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was ground with acetonitrile (10 mL) to afford 2-morpholino-2-phenylacetic acid hydrochloride as a white solid (0.22 g, 63.7% yield).1H NMR (300 MHz, DMSO-d6) δ 11.79 (s, 1H), 7.56-7.72 (m, 2H), 7.37-7.56 (m, 3H) , 5.25 (s, 1H), 3.60-4.10 (m, 4H), 3.27 (br.s, 2H), 2.96 (br.s, 2H).

22083-23-4
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91641-50-8
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Yield:91641-50-8 63.7%

Reaction Conditions:

with hydrogenchloride;water in 1,4-dioxane;Reflux;

Steps:

12 Preparation of 2-morpholino-2-phenylacetic acid hydrochloride (139).

Preparation of 2-morpholino-2-phenylacetic acid hydrochloride (139). Ethyl 2-moφholino-2-phenylacetate (0.34 g, 1.36 mmol) was dissolved in dioxane (1 1.4 ml) and 37% HCl (1.1 ml, 13.6 mmol) was added dropwise. The mixture was stirred at reflux overnight. 37% HCl (1.1 ml, 13.6 mmol) was added and the reaction was refluxed for additional 24 h. The solvent was evaporated and the residue was triturated with acetonitrile (10 ml) to obtain 2-moφholino-2-phenylacetic acid hydrochloride (0.22 g, 63.7 % yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) ppm 1 1.79 (s, 1 H), 7.56 - 7.72 (m, 2 H), 7.37 - 7.56 (m, 3 H), 5.25 (s, 1 H), 3.60 - 4.10 (m, 4 H), 3.27 (br. s., 2 H), 2.96 (br. s., 2 H).

References:

WO2013/98145,2013,A1 Location in patent:Page/Page column 50