Benzyl Bromide → N-(1-benzylpiperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

HRID 1978460Notes

Reaction equation

HRID 1978460 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.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)C>[CH2:32]([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)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 21993937N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 1

HCID 21994006N-(1-benzylpiperidin-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 was added 0.19 ml (1.6 mM) of benzyl bromide at room temperature, and the mixture was refluxed under nitrogen for 6 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 MgSO4. The resulting crude product was purified by column chromatography (methanol/ethyl acetate 40%) to provide the title compound.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 6 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 MgSO4
  7. customThe resulting crude product was purified by column chromatography (methanol/ethyl acetate 40%)

Sources & evidence

ORD record
ord-a97cbf7ba0864a13b0b686865d8f609e
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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