Potassium Hydroxide → HCID 70510120, compound

HRID 1285346Notes

Reaction equation

HRID 1285346 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[OH-].[K+].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl>CS(C)=O>[ClH:22].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])[C:12]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 15593400HCID 15593400, compound

Product 1

HCID 70510120HCID 70510120, compoundYield 149.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 6.72 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 2.58 g of potassium hydroxide and 90 ml of dimethylsulfoxide is stirred at room temperature for one hour. Then, 3.16 g of 2-(dimethylamino)ethyl chloride hydrochloride are added to the mixture, and said mixture is stirred at room temperature for 16 hours. The reaction mixture is poured into ice-water, and the precipitated crystals are collected by filtration and washed with water. The crystals are dissolved in concentrated hydrochloric acid, and the solution is washed with ethyl acetate and then alkalized with potassium carbonate. Then, the solution is extracted with chloroform. The extract is washed with water, dried and then evaporated to remove solvent. The residue is converted to its hydrochloride and then recrystallized from ethanol. 6.65 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride are thereby obtained. Recrystallization of the product from a mixture of chloroform, ethanol and ether gives crystals (prisms) melting at 136°-139° C.

Workup

  1. stirringis stirred at room temperature for 16 hours
  2. filtrationthe precipitated crystals are collected by filtration
  3. washwashed with water
  4. dissolutionThe crystals are dissolved in concentrated hydrochloric acid
  5. washthe solution is washed with ethyl acetate
  6. extractionThen, the solution is extracted with chloroform
  7. washThe extract is washed with water
  8. customdried
  9. customevaporated
  10. customto remove solvent
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-00aaa291aa91466eb9c1224517b34939
Source dataset
uspto-grants-1986_01
Patent number
US04567175

Reaction notes

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