1-Methylpiperazine → 5-[4-(4-methylpiperazin-1-yl)-1,4-dioxo-3-(phenylmethyl)butyl]-5,6-dihydro-4H-thieno[3,4-c]pyrrole

HRID 362470Notes

Reaction equation

HRID 362470 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[O:13]=[C:14]([N:27]1[CH2:31][C:30]2=[CH:32][S:33][CH:34]=[C:29]2[CH2:28]1)[CH2:15][CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17]([OH:19])=O.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>O1CCCC1>[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:17](=[O:19])[CH:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][C:14]([N:27]2[CH2:31][C:30]3=[CH:32][S:33][CH:34]=[C:29]3[CH2:28]2)=[O:13])[CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 682631,1'-CarbonyldiimidazoleHCID 15337447gamma-oxo-alpha-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoic acid

Product 1

HCID 675737185-[4-(4-methylpiperazin-1-yl)-1,4-dioxo-3-(phenylmethyl)butyl]-5,6-dihydro-4H-thieno[3,4-c]pyrroleYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.55 g (3.39 mmol) of carbonyldiimidazole is added to a solution of 1 g (3.17 mmol) of γ-oxo-α-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoic acid in 15 ml of dry tetrahydrofuran. The solution is stirred at room temperature for 1 h and then 0.42 ml (3.8 mmol) of 4-methylpiperazine is added and the solution is stirred at room temperature for 20 h. The mixture is then evaporated to dryness, the residue is dissolved in 50 ml of dichloromethane, and then the solution obtained is washed successively with twice 50 ml of a saturated sodium hydrogen carbonate solution and 20 ml of a saturated sodium chloride solution, dried over sodium sulphate and then evaporated to dryness. After recrystallization from ethanol, 1 g of a white solid is obtained.

Workup

  1. stirringthe solution is stirred at room temperature for 20 h
  2. customThe mixture is then evaporated to dryness
  3. dissolutionthe residue is dissolved in 50 ml of dichloromethane
  4. customthe solution obtained
  5. washis washed successively with twice 50 ml of a saturated sodium hydrogen carbonate solution and 20 ml of a saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness
  8. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-45f660b67d8d496da55afae62f216aa8
Source dataset
uspto-grants-1999_02
Patent number
US05869518

Reaction notes

Loading…