1-Phenylpiperazine → 4-(4-Phenylpiperazinyl)butyl-2,3,4,5-tetrahydro-1,4-benzothiazepine-3,5-dione

HRID 1033711Notes

Reaction equation

HRID 1033711 reaction equation
BrCCCC[N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[S:9][CH2:8][C:7]1=[O:18].[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[C:19]1([N:25]2[CH2:30][CH2:29][N:28]([CH2:17][CH2:10][CH2:11][CH2:12][CH:8]3[C:7](=[O:18])[NH:6][C:12](=[O:13])[C:11]4[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=4[S:9]3)[CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 15233924HCID 15233924, compound

Product 1

HCID 1317184044-(4-Phenylpiperazinyl)butyl-2,3,4,5-tetrahydro-1,4-benzothiazepine-3,5-dioneYield 197.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 115 mg of compound of Example 13 dissolved in 10 ml of dioxane was added 171 mg (3 equivalents) of N-phenylpiperazine, followed by heating under reflux for 4 hours. Next, dioxane was evaporated, aqueous sodium bicarbonate added and the mixture extracted with methylene chloride. After washing the extract with aqueous sodium chloride, the mixture was dried over anhydrous magnesium sulfate. Next, the residue obtained by concentration of the methylene chloride solution was purified by silica gel column chromatography (ethyl acetate:hexane=3:1) to obtain 142 mg of the desired compound (yield 99.0%). The fumarate was obtained by converting the product to a fumarate in a conventional manner, followed by recrystallization from acetone-ether.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. customNext, dioxane was evaporated
  4. additionaqueous sodium bicarbonate added
  5. extractionthe mixture extracted with methylene chloride
  6. washAfter washing the
  7. extractionextract with aqueous sodium chloride
  8. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  9. customNext, the residue obtained by concentration of the methylene chloride solution
  10. customwas purified by silica gel column chromatography (ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-682a65ee0da440f9954bb471c60d311f
Source dataset
uspto-grants-1994_05
Patent number
US05312625

Reaction notes

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