Potassium Carbonate → HCID 11004065, compound

HRID 1285342Notes

Reaction equation

HRID 1285342 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.Cl.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(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]([CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])[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 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 15593400HCID 15593400, compound

Product 1

HCID 11004065HCID 11004065, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.8 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 3.02 g of 2-(dimethylamino)ethyl chloride hydrochloride, 6.1 g of potassium carbonate and 150 ml of acetone is refluxed for 20 hours. After the reaction is completed, insoluble materials are removed by filtration and washed with ethanol. The washings are added to the filtrate, and the combined solution is evaporated under reduced pressure to remove solvent. The residue is dissolved in ethyl acetate, and the solution is washed with water, dried and then evaporated to remove solvent. The residue is recrystallized from a mixture of ethyl acetate and n-hexane. 7.13 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are thereby obtained as colorless needles.

Workup

  1. temperatureis refluxed for 20 hours
  2. custominsoluble materials are removed by filtration
  3. washwashed with ethanol
  4. additionThe washings are added to the filtrate
  5. customthe combined solution is evaporated under reduced pressure
  6. customto remove solvent
  7. dissolutionThe residue is dissolved in ethyl acetate
  8. washthe solution is washed with water
  9. customdried
  10. customevaporated
  11. customto remove solvent
  12. customThe residue is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-3dd6f6d4751044619b31619ccc1aff7b
Source dataset
uspto-grants-1986_01
Patent number
US04567175

Reaction notes

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