Potassium Carbonate → (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1247991Notes

Reaction equation

HRID 1247991 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[C@@H:21]([OH:22])[C:20](=[O:23])[NH:19][C:18]3[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=3[S:16]2)=[CH:11][CH:10]=1.Cl.[CH3:29][N:30]([CH2:34][CH2:35]Cl)[CH2:31][CH2:32][CH3:33]>CC(C)=O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]2[C@@H:21]([OH:22])[C:20](=[O:23])[N:19]([CH2:35][CH2:34][N:30]([CH3:29])[CH2:31][CH2:32][CH3:33])[C:18]3[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=3[S:16]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-HCID 30312081-Propanamine, N-(2-chloroethyl)-N-methyl-, hydrochloride

Product 1

HCID 70381919(+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 92.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.05 g of potassium carbonate are added to a mixture of 10.0 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 6.57 g of 2-(N-methyl-N-n-propylamino)ethyl chloride hydrochloride and 100 ml of acetone. The mixture is refluxed under stirring overnight. After the reaction, the mixture is treated in the same manner as described in Example 28-(1). 12.3 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are thereby obtained as an oil. Yield: 92%.

Workup

  1. temperatureThe mixture is refluxed
  2. customAfter the reaction
  3. additionthe mixture is treated in the same manner

Sources & evidence

ORD record
ord-52fa4b6e9891442b8d57b9d0a020d43e
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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