Potassium Carbonate → HCID 11004065, compound

HRID 654661Notes

Reaction equation

HRID 654661 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 (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (6.8 g), 2-(dimethylamino)ethyl chloride hydrochloride (3.02 g), potassium carbonate (6.1 g) and acetone (150 ml) is stirred under refluxing for 20 hours. After the completion of the reaction, the insoluble materials are removed by filtration and the filtrate is concentrated under reduced pressure. The resulting residue is dissolved in ethyl acetate, washed with water, dried and the ethyl acetate is distilled off. The resulting residue is recrystallized from a mixture of ethyl acetate and n-hexane to give (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (7.13 g) as colorless needles, m.p. 122°-124° C. (decomposed).

Workup

  1. temperatureunder refluxing for 20 hours
  2. customAfter the completion of the reaction
  3. customthe insoluble materials are removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. dissolutionThe resulting residue is dissolved in ethyl acetate
  6. washwashed with water
  7. customdried
  8. distillationthe ethyl acetate is distilled off
  9. customThe resulting residue is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-6bbf57bc04be4ff9b5c8005032b086f3
Source dataset
uspto-grants-1992_07
Patent number
US05134139

Reaction notes

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