Potassium Hydroxide → (2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochloride

HRID 1903700Notes

Reaction equation

HRID 1903700 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][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][Cl:27].[OH-].[K+].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.C(O)C>C(O)C.CC(C)=O>[ClH:27].[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]([CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 21887872Ethanol hydrochloride

Product 1

HCID 12449428(2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochlorideYield 86.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 30.1 g of cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one, 17.8 g of 2-(dimethylamino)ethyl chloride hydrochloride, 13.7 g of 96% potassium hydroxide, 60 g of sodium sulfate and 300 ml of acetone is stirred at 50° C. for 7 hours. After the reaction is completed, the mixture is filtered to remove inorganic materials and the filtrate is condensed. The residue is dissolved in ethanol. After cooling the solution, 10% HCl/ethanol is added thereto. The crystalline precipitates are collected by filtration and then dried. 35.1 g of cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepine-4(5H)-one hydrochloride are thereby obtained. Yield: 86.2%

Workup

  1. filtrationthe mixture is filtered
  2. customto remove inorganic materials
  3. customcondensed
  4. additionis added
  5. customThe crystalline precipitates
  6. filtrationare collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-75d2890cfa964a9c89e8ea377c8a8d0c
Source dataset
uspto-grants-1984_03
Patent number
US04438035

Reaction notes

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