Potassium Hydroxide → HCID 70410110, compound

HRID 280518Notes

Reaction equation

HRID 280518 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]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[OH-].[K+].Cl.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]Cl>CS(C)=O>[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]([CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])[C:12]3[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[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 70481959HCID 70481959, compound

Product 1

HCID 70410110HCID 70410110, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 0.828 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-7-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 0.307 g of potassium hydroxide and 15 ml of dimethylsulfoxide is stirred at room temperature for 2 hours, and then 0.396 g of 2-(dimethylamino)ethyl chloride hydrochloride is added thereto. The mixture is stirred at room temperature for 16 hours. After the reaction is completed, the mixture is poured into ice-water, and the aqueous solution is extracted with ethyl acetate. The ethyl acetate solution is extracted with a 10% hydrochloric acid solution. The extract is adjusted to about pH 10 with potassium carbonate. The alkaline solution is extracted witn ethyl acetate, and the extract is washed with water, dried and then evaporated to remove solvent. The residue is recrystallized from a mixture of ethyl acetate and n-hexane. 0.82 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-7-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is obtained. Yield: 82%

Workup

  1. stirringThe mixture is stirred at room temperature for 16 hours
  2. extractionthe aqueous solution is extracted with ethyl acetate
  3. extractionThe ethyl acetate solution is extracted with a 10% hydrochloric acid solution
  4. extractionThe alkaline solution is extracted witn ethyl acetate
  5. washthe extract is washed with water
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-898491713f8749128804bdc296003772
Source dataset
uspto-grants-1986_05
Patent number
US04590188

Reaction notes

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