Triethylamine → N-[1-(phenylaminocarbonylmethyl)-piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

HRID 1978469Notes

Reaction equation

HRID 1978469 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.Cl[CH2:33][C:34]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35]>C(O)C>[C:37]1([NH:36][C:34]([CH2:33][N:3]2[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([C:13]3[S:23][C:22]4[N:24]5[C:15](=[CH:16][N:17]=[C:18]5[CH:19]=[CH:20][CH:21]=4)[CH:14]=3)=[O:12])[CH2:5][CH2:4]2)=[O:35])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11485ChloroacetanilideHCID 21993937N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 1

HCID 70246692N-[1-(phenylaminocarbonylmethyl)-piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 581 mg (1.5 mM) of N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride and 759 mg (7.5 mM) of triethylamine in ethanol (30 ml) was added 254 mg (1.5 mM) of chloroacetylaniline at room temperature, and the mixture was refluxed for 18 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over Na2SO4. The resulting crude product was purified by column chromatography (methanol/ethyl acetate=½) to provide the title compound as red oil.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over Na2SO4
  7. customThe resulting crude product was purified by column chromatography (methanol/ethyl acetate=½)

Sources & evidence

ORD record
ord-1cab7972edb541cbb19a37608a05989c
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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