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

HRID 1978465
Notes
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Reaction equation

HRID 1978465 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.[O:32]([CH2:39][CH2:40][CH2:41][CH2:42]Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)C>[O:32]([CH2:39][CH2:40][CH2:41][CH2:42][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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70986(4-Bromobutoxy)benzene2×HCID 21993937N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 1

HCID 21993919N-[1-(4-phenoxybutan-1-yl)piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

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 (27.5 mM) of triethylamine in ethanol (6 ml) was added 0.45 g (1.96 mM) of 4-phenoxybutyl bromide at room temperature and the mixture was refluxed under nitrogen for 14 hours. To this reaction mixture was further added 0.23 g (1.0 mM) of 4-phenoxybutyl bromide and the mixture was refluxed for 6 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/chloroform=1/15-1/10-1/5) to provide the title compound.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 14 hours
  2. temperaturethe mixture was refluxed for 6 hours
  3. distillationThe solvent was then distilled off under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over MgSO4
  8. customThe resulting crude product was purified by column chromatography (methanol/chloroform=1/15-1/10-1/5)

Sources & evidence

ORD record
ord-856e361ad1614b739ec555ac5effb5fb
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06235731B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes