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

HRID 1978482
Notes
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Reaction equation

HRID 1978482 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[S:22][C:21]3[N:23]4[C:14](=[CH:15][N:16]=[C:17]4[CH:18]=[CH:19][CH:20]=3)[CH:13]=2)=[O:11])[CH2:5][CH2:4]1.C(N(CC)CC)C.I[CH2:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(O)C.O>[C:36]1([CH2:35][CH2:34][CH2:33][CH2:32][N:3]2[CH2:4][CH2:5][CH:6]([NH:9][C:10]([C:12]3[S:22][C:21]4[N:23]5[C:14](=[CH:15][N:16]=[C:17]5[CH:18]=[CH:19][CH:20]=4)[CH:13]=3)=[O:11])[CH2:7][CH2:8]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12709818(4-Iodobutyl)benzeneHCID 21994154N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 1

HCID 21993651N-[1-(4-phenylbutan-1-yl)piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962WaterSolvent

Procedure

To a solution of 72.5 mg (1.94 mM) of N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride and 1.4 ml (10.0 mM) of triethylamine in ethanol (7 ml) was added 0.61 g (2.33 mM) of 1-iodo-4-phenylbutane at room temperature and the mixture was refluxed under nitrogen for 6 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over MgSO4, and concentrated. The resulting crude product was purified by column chromatography (methanol/ethyl acetate 30%) and recrystallization from ethyl acetate to provide the title compound as light-purple crystals.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting crude product was purified by column chromatography (methanol/ethyl acetate 30%) and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3900d9725ea54d25a5297574ead1d172
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