methyl 4-(1-aminopropan-2-yl)benzoate hydrochloride synthesis

Yield:1220904-21-1 68%

Reaction Conditions:

with hydrogenchloride;palladium 10% on activated carbon;hydrogen in ethanol;lithium hydroxide monohydrate;

Steps:

1.1.2

To a solution of methyl 4-(l-cyanoethyl)benzoate (Int i-4, 12.4 g, 65.5 mmol) in EtOH (100 mL) was added concentrated HCI (20 mL). 10% Pd/C (3.4 g) was added and the resulting mixture was stirred under a hydrogen atmosphere overnight. The mixture was then filtered over Celite and further 10% Pd/C (3.4 g) was added and the mixture was again stirred overnight under a hydrogen atmosphere. The process of filtration over Celite, retreatment with 10% Pd/C and hydrogenation was repeated twice more until complete reaction was observed. The mixture was then filtered over Celite and concentrated at reduced pressure. The residue obtained was slurried in MTBE (200 mL) with rapid stirring for 1 h. The solids obtained were filtered and dried giving the title compound (10.2 g, 68% yield) as a white solid. LCMS (Method D) rt = 0.72 min, MS (ESIPos) m/z=194 (M+H)⁺.

References:

WO2022/128850,2022,A1 Location in patent:Paragraph 0223; 0226; 0228