Potassium Carbonate → HCID 70381657, compound

HRID 1247993Notes

Reaction equation

HRID 1247993 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]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C.O>[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][CH2:25][N:24]([CH3:29])[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

7

Reactant 3

HCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-

Product 1

HCID 70381657HCID 70381657, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.01 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 1.74 g of 3-(dimethylamino)propyl chloride hydrochloride are dissolved in 30 ml of acetone, and 3.04 g of potassium carbonate are added thereto. The mixture is refluxed overnight under stirring. After the reaction, the mixture is condensed under reduced pressure, and the residue is dissolved in ethyl acetate and water. The ethyl acetate layer is collected, dried and then evaporated to remove solvent. 3.3 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[3-(dimethylamino)-propyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are thereby obtained as an oil.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. customAfter the reaction
  3. customcondensed under reduced pressure
  4. customThe ethyl acetate layer is collected
  5. customdried
  6. customevaporated
  7. customto remove solvent

Sources & evidence

ORD record
ord-e65e46e771364f6ba777e284f066488e
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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