ChemicalBook CAS DataBase List DESACETYL DILTIAZEM HCL

DESACETYL DILTIAZEM HCL synthesis

4synthesis methods

Product Name:DESACETYL DILTIAZEM HCL
CAS Number:75472-91-2
Molecular formula:C20H25ClN2O3S
Molecular Weight:408.94

2-Dimethylaminoethyl chloride hydrochloride

4584-46-7
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(2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

42399-49-5
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75472-91-2
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Yield:75472-91-2 88%

Reaction Conditions:

with water;potassium carbonate in ethyl acetate; for 12 h;Heating / reflux;

Steps:

2.c

A flame-dried two-necked 25 mL round-bottomed flask was charged with cyclic sulfite (1 mmol), Fe3+-clay (100 mg) and dry xylene (5 mL) and stirred under a constant flush of nitrogen. Freshly distilled 2-aminothiophenol (0.9 mmol) was added drop wise, and the reaction mixture was refluxed for 12 h. Crude compound was chromatographed to get cis-(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (50% yield). The hydroxy lactam (0.54 mmol) was dissolved in ethyl acetate (5 mL) and 2-(dimethylamino) ethyl chloride hydrochloride (0.694 mmol) was added followed by addition of finely ground K2CO3 (2.16 mmol) and a drop of water. The heterogeneous mixture was stirred at reflux for 12 h. Solvent was removed and the crude product was chromatographed to obtain N-alkylated product (88%).

References:

US2004/127704,2004,A1 Location in patent:Page 3

2-Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, 1,1-dimethylethyl ester, (2R,3S)-

201804-22-0
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75472-91-2
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Benzenepropanoic acid, β-[(2-aminophenyl)thio]-α-hydroxy-4-methoxy-, 1,1-dimethylethyl ester, (αS,βS)-

201804-23-1
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75472-91-2
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1-Propanone, 1-[(2R,3S)-3-(4-methoxyphenyl)-2-oxiranyl]-2,2-dimethyl-

201804-19-5
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75472-91-2
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References