Potassium Carbonate → HCID 18980218, compound

HRID 2392575Notes

Reaction equation

HRID 2392575 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[CH:8][S:7][C:6]=2[CH:16]=1.Br[CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]4[C:26](=[O:27])[C:25]5[C:24](=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:23]4=[O:32])[CH2:14][CH2:15]3)=[CH:8][S:7][C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 10609857HCID 10609857, compound

Product 1

HCID 18980218HCID 18980218, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(6-fluorobenzo[b]thien-3-yl)-piperazine (20.0 g, 84.6 mmol), N-(4-bromobutyl)phthalimide (26.3 g, 93.2 mmol), anhydrous potassium carbonate (17.5 g, 127 mmol), KI (1.40 g, 8.43 mmol), and anhydrous acetonitrile (500 mL) was stirred at reflux for 17 hours. The thick slurry was filtered, the insolubles washed with chloroform (2×100 mL), and the filtrate concentrated in vacuo. The residue was taken up in chloroform (400 mL), washed with water (200 mL), and dried (MgSO4). The solvent was removed in vacuo and the product chromatographed on silica gel, with 20% heptane/ethyl acetate as eluent, to afford 25.8 g of a yellow solid. Recrystallization from ether afforded 10.9 g (29%) of the title compound as a yellow powder: m.p.=94°-95° C.

Workup

  1. temperatureat reflux for 17 hours
  2. filtrationThe thick slurry was filtered
  3. washthe insolubles washed with chloroform (2×100 mL)
  4. concentrationthe filtrate concentrated in vacuo
  5. washwashed with water (200 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe product chromatographed on silica gel, with 20% heptane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-e30b725671014dc59b5031e748cfcf2c
Source dataset
uspto-grants-1998_09
Patent number
US05801176

Reaction notes

Loading…