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 1247987Notes

Reaction equation

HRID 1247987 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])[N:13]([CH2:18][CH2:19][NH:20][CH3:21])[C:12]3[CH:22]=[CH:23][CH:24]=[CH:25][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[CH2:26](I)[CH2:27]C.[C:30](=O)([O-])[O-].[K+].[K+]>CN(C)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]([CH2:18][CH2:19][N:20]([CH3:30])[CH2:21][CH2:26][CH3:27])[C:12]3[CH:22]=[CH:23][CH:24]=[CH:25][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 1589451,5-Benzothiazepin-4(5H)-one, 2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-(2-(methylamino)ethyl)-, (2S,3S)-

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)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(methylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 1.0 g of n-propyl iodide are dissolved in 25 ml of dimethylformamide, and 1.16 g of potassium carbonate are added thereto. The mixture is stirred at room temperature for 4 hours. After the reaction, the mixture is poured into ice-water and then extracted with ethyl acetate. The extract is washed with water, dried and then condensed, whereby (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is obtained as a colorless oil.

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customcondensed

Sources & evidence

ORD record
ord-df9d29de31994fa892e877462a1c6f27
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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