Potassium Carbonate → HCID 70430585, compound

HRID 978343Notes

Reaction equation

HRID 978343 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[NH:13][C:12]3[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH2:2].[ClH:25].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[N:13]([CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])[C:12]3[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 70460882HCID 70460882, compound

Product 1

HCID 70430585HCID 70430585, compoundYield 169.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 200 mg of (±)-cis-2-(4-methoxyphenyl)-3-acetoxy-9-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 84 mg of 2-(dimethylamino)ethyl chloride hydrochloride, 220 mg of powdered potassium carbonate and 10 ml of acetone is refluxed for 20 hours. After the reaction is completed, insoluble materials are removed by filtration. The filtrate is evaporated to remove solvent. The residue is converted to its hydrochloride and then recrystallized from methanol. 226 mg of (±)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(dimethylamino)ethyl]-9-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride hydrate are obtained. Yield: 85%

Workup

  1. temperatureis refluxed for 20 hours
  2. custominsoluble materials are removed by filtration
  3. customThe filtrate is evaporated
  4. customto remove solvent
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5d7202c0173646dfb17877842fc88fe4
Source dataset
uspto-grants-1987_05
Patent number
US04665068

Reaction notes

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