Sodium Iodide → N-[1-(3-(2-fluorophenoxy)propan-1-yl)piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

HRID 1978467Notes

Reaction equation

HRID 1978467 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([C:13]2[S:23][C:22]3[N:24]4[C:15](=[CH:16][N:17]=[C:18]4[CH:19]=[CH:20][CH:21]=3)[CH:14]=2)=[O:12])[CH2:5][CH2:4]1.C(N(CC)CC)C.[F:32][C:33]1[CH:43]=[CH:42][CH:41]=[CH:40][C:34]=1[O:35][CH2:36][CH2:37][CH2:38]Cl.[I-].[Na+]>C(O)C>[F:32][C:33]1[CH:43]=[CH:42][CH:41]=[CH:40][C:34]=1[O:35][CH2:36][CH2:37][CH2:38][N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([C:13]2[S:23][C:22]3[N:24]4[C:15](=[CH:16][N:17]=[C:18]4[CH:19]=[CH:20][CH:21]=3)[CH:14]=2)=[O:12])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 30182221-(3-Chloropropoxy)-2-fluorobenzeneHCID 21993937N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 1

HCID 21994003N-[1-(3-(2-fluorophenoxy)propan-1-yl)piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.58 g (1.5 mM) of N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride and 1.0 ml (7.5 mM) of triethylamine in ethanol were added 0.37 g (2.0 mM) of 3-(2-fluorophenoxy)-propyl chloride and 0.28 g (1.9 mM) of sodium iodide at room temperature and the mixture was refluxed under nitrogen for 20 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The resulting crude product was purified by column chromatography (methanol/ethyl acetate 30-50%) to provide the title compound.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 20 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over MgSO4
  7. customThe resulting crude product was purified by column chromatography (methanol/ethyl acetate 30-50%)

Sources & evidence

ORD record
ord-6ddff7085f5f49b5913a8f6f91f6362b
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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