Potassium Carbonate → HCID 70455044, compound

HRID 1381143Notes

Reaction equation

HRID 1381143 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][C:23]([Cl:25])=[CH:24][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH2:27]([N:34]([CH2:36][CH2:37]Cl)[CH3:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[N:13]([CH2:37][CH2:36][N:34]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH3:35])[C:12]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12822620N-(2-Chloroethyl)-N-methylbenzylamine hydrochlorideHCID 70453288HCID 70453288, compound

Product 1

HCID 70455044HCID 70455044, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.0 g of (-)-cis-2-(4-methoxyphenyl)-3-acetoxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 1.9 g of 2-(N-benzyl-N-methylamino)ethyl chloride.hydrochloride, 3.3 g of potassium carbonate and 80 ml of acetone is refluxed for 20 hours. Insoluble materials are removed by filtration, and the filtrate is evaporated under reduced pressure to remove solvent. The residue is dissolved in ethyl acetate, and the solution is washed with water, dried and evaporated to remove solvent. 2.9 g of (-)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(N-benzyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained as an oil.

Workup

  1. temperatureis refluxed for 20 hours
  2. customInsoluble materials are removed by filtration
  3. customthe filtrate is evaporated under reduced pressure
  4. customto remove solvent
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washthe solution is washed with water
  7. customdried
  8. customevaporated
  9. customto remove solvent

Sources & evidence

ORD record
ord-bb574e6331414e3a91b3cddf1199dc33
Source dataset
uspto-grants-1986_04
Patent number
US04585768

Reaction notes

Loading…