Triethylamine → HCID 21993797, compound

HRID 1978478Notes

Reaction equation

HRID 1978478 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([CH: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)[CH2:14]2)=[O:12])[CH2:5][CH2:4]1.C(N(CC)CC)C.Br[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][N:3]2[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([CH: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)[CH2:14]3)=[O:12])[CH2:5][CH2:4]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzeneHCID 21994023HCID 21994023, compound

Product 1

HCID 21993797HCID 21993797, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 746.4 mg (1.91 mM) of N-(4-piperidyl)methyl-3,4-dihydro-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride and 1.4 ml (10.0 mM) of triethylamine in ethanol (5 ml) was added 0.35 ml (2.30 mM) of 1-bromo-3-phenylpropane at room temperature and the mixture was refluxed under nitrogen for 64 hours. This reaction mixture was diluted with water and extracted with chloroform, and the organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The residue was purified by column chromatography (methanol/ethyl acetate 20-30-50%) to provide the title compound as red amorphous substance.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 64 hours
  2. extractionextracted with chloroform
  3. washthe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over MgSO4
  5. customThe residue was purified by column chromatography (methanol/ethyl acetate 20-30-50%)

Sources & evidence

ORD record
ord-621736c7a5234c9fb167cabf44738f77
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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