Potassium Carbonate → HCID 86740805, compound

HRID 280517Notes

Reaction equation

HRID 280517 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[C:18]([CH3:22])=[CH:19][CH:20]=[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:4]=[CH:5][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[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 70483781HCID 70483781, compound

Product 1

HCID 86740805HCID 86740805, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.81 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-6-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 1.35 g of 2-(dimethylamino)ethyl chloride hydrochloride, 2.7 g of potassium carbonate and 40 ml of acetone is refluxed for 16 hours. After the reaction is completed, the inorganic materials are removed by filtration and then washed with chloroform. The filtrate and the washing are combined and then evaporated to remove solvent. The residue is converted into its hydrochloride and then recrystallized from a mixture of ethanol and ether. 2.93 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-6-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride 3/4 hydrate are obtained. Yield: 77%

Workup

  1. temperatureis refluxed for 16 hours
  2. customthe inorganic materials are removed by filtration
  3. washwashed with chloroform
  4. customevaporated
  5. customto remove solvent
  6. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-f5fbb4df5cdf4407bdfd2c22c71c33c9
Source dataset
uspto-grants-1986_05
Patent number
US04590188

Reaction notes

Loading…