2-Chloro-N,N-dimethylethylamine → 3-(Acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

HRID 1649327Notes

Reaction equation

HRID 1649327 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[NH:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:27][N:28]([CH2:30][CH2:31]Cl)[CH3:29].C(OC(C)C)(C)C>CCOCC.C(O)(=O)C.CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[N:13]([CH2:31][CH2:30][N:28]([CH3:29])[CH3:27])[C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 79012-Chloro-N,N-dimethylethylamineHCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 591255Benzo[b][1,4]thiazepin-4(5H)-one, 2,3-dihydro-3-acetoxy-2-(4-methoxyphenyl)-2×

Product 1

HCID 30763-(Acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-oneYield 76.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

5-(1). 2-(4'-Methoxyphenyl)-3-acetoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one [Compound (II)] (1.0 g) and dried silica gel suitable for column chromatography (which is obtained by calcining a commercially available silica gel (Wako gel C-200) at 300° C. under nitrogen for 8 hours) (0.5 g) are added to dimethylsulfoxide (10 ml), and thereto is added a 60% by weight sodium hydride (0.14 g), and the mixture is stirred at room temperature for 30 minutes. A 50% by weight solution (0.75 g) of N,N-dimethylaminoethyl chloride in ether is added to the mixture, and the mixture is further stirred at room temperature for 5 hours and neutralized with acetic acid, and then, silica gel is filtered off. To the filtrate is added benzene, and the benzene solution is washed with water, dried, and evaporated to remove benzene to give a solid substance (1.20 g). The solid substance is added to diisopropyl ether. After removing the insoluble materials by filtration, the filtrate is allowed to stand at room temperature. The precipitated crystals are separated by filtration to give the title compound (I) (0.92 g, 76.2%), m.p. 134°-135° C. The hydrochloride of this product: m.p. 187°-188° C.

Workup

  1. customat 300° C.
  2. customfor 8 hours
  3. stirringthe mixture is further stirred at room temperature for 5 hours
  4. filtrationsilica gel is filtered off
  5. additionTo the filtrate is added benzene
  6. washthe benzene solution is washed with water
  7. customdried
  8. customevaporated
  9. customto remove benzene
  10. customto give a solid substance (1.20 g)
  11. customAfter removing the insoluble materials
  12. filtrationby filtration
  13. customto stand at room temperature
  14. customThe precipitated crystals are separated by filtration

Sources & evidence

ORD record
ord-eeda6be577fb445ab2a11dcf28ecfe20
Source dataset
uspto-grants-1983_11
Patent number
US04416819

Reaction notes

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