Potassium Carbonate → HCID 70482384, compound

HRID 280525Notes

Reaction equation

HRID 280525 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]([F: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:28].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[ClH:28].[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]([F: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 70482562HCID 70482562, compound

Product 1

HCID 70482384HCID 70482384, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 1.99 g of 2-(dimethylamino)ethyl chloride hydrochloride, 4.3 g of potassium carbonate and 50 ml of acetone is refluxed for 18 hours. After the reaction is completed, insoluble materials are removed by filtration and washed with hot acetone. The filtrate and the washings are combined and then evaporated to remove solvent. The residue is converted to its hydrochloride and recrystallized from a mixture of isopropanol, ethanol and ether. 4 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-8-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride are obtained.

Workup

  1. temperatureis refluxed for 18 hours
  2. custominsoluble materials are removed by filtration
  3. washwashed with hot acetone
  4. customevaporated
  5. customto remove solvent
  6. customrecrystallized from a mixture of isopropanol, ethanol and ether

Sources & evidence

ORD record
ord-821a48a661be4e60b2f29ae784fba784
Source dataset
uspto-grants-1986_05
Patent number
US04590188

Reaction notes

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