ChemicalBook CAS DataBase List FEXOFENADINE HYDROCHLORIDE

FEXOFENADINE HYDROCHLORIDE synthesis

9synthesis methods

Product Name:FEXOFENADINE HYDROCHLORIDE
CAS Number:138452-21-8
Molecular formula:C32H40ClNO4
Molecular Weight:538.12

Methyl-4-4(4-hydroxy diphenyl-methyl)-piperidine-1-oxobutyl-2-2-dimethyl phenyl

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Yield:138452-21-8 88.5%

Reaction Conditions:

Stage #1: 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid, methyl esterwith methanol;sodium tetrahydridoborate at 5 - 30; for 1 h;Large scale;
Stage #2: with lithium hydroxide monohydrate;sodium hydroxide for 4 h;Reflux;Large scale;
Stage #3: with hydrogenchloride in lithium hydroxide monohydrate at 10; pH=2.5; for 2 h;Large scale;Temperature;

Steps:

1.4-1.5; 5-9

Add 110kg of methanol to the 200L reaction kettle, add 14kg of intermediate III under stirring, control the temperature to 5°C, add 1.06kg of sodium borohydride in batches, after the addition, heat up to 20-30°C and continue the reaction for 1h, add 21kg of hydrogen Sodium oxide solution (4.2kg sodium hydroxide+16.8kg purified water), heat up to reflux reaction, until dissolved and clear (about 4h), add 0.2kg activated carbon and continue to reflux for 0.5h, filter, cool the filtrate to 10 , add 6mol dropwise /L hydrochloric acid solution, adjust pH=2.5, add 94kg of purified water, continue to stir for 2h, a large amount of solids are precipitated, centrifuge to obtain wet product, the wet product is placed in a vacuum drying box, and dried at 50 ~ 60 to obtain 13.1kg of fexofil hydrochloride That would be crude.The molar yield was 89.5%.Add 67kg of acetone to the 200L reactor, add 13kg of fexofenadine hydrochloride crude product under stirring, heat up to reflux for 3h, drop to room temperature, centrifuge, and dry the filter cake at 50-60°C in a vacuum drying oven to obtain fexofenadine hydrochloride The final product is about 11.5kg.The molar yield was 88.5%.

References:

CN114539131,2022,A Location in patent:Paragraph 0062; 0069-0074; 0088-0107