Triethylamine → HCID 21993694, compound

HRID 1978450Notes

Reaction equation

HRID 1978450 reaction equation
Cl.Cl.[NH:3]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[S:21][C:20]3[N:22]4[C:13](=[CH:14][N:15]=[C:16]4[CH:17]=[CH:18][CH:19]=3)[CH:12]=2)=[O:10])[CH2:4]1.C(N(CC)CC)C.Br[CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)C>[C:34]1([CH2:33][CH2:32][CH2:31][N:3]2[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]3[S:21][C:20]4[N:22]5[C:13](=[CH:14][N:15]=[C:16]5[CH:17]=[CH:18][CH:19]=4)[CH:12]=3)=[O:10])[CH2:4]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzene2×HCID 21993812HCID 21993812, compound

Product 1

HCID 21993694HCID 21993694, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.50 g (1.39 mM) of N-(3-pyrrolidinyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride and 1.0 ml (7.17 mM) of triethylamine in ethanol (5 ml) was added 0.25 ml (1.64 mM) of 1-bromo-3-phenylpropane at room temperature, and the mixture was refluxed under nitrogen for 18 hours. To this reaction mixture was further added 0.2 ml (1.32 mM) of 1-bromo-3-phenylpropane, and the mixture was further refluxed for 3 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, dried over MgSO4, and purified by column chromatography (methanol/ethyl acetate 20-30%) to provide N-[1-(3-phenylpropan-1-yl)pyrrolidin-3-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 18 hours
  2. temperaturethe mixture was further refluxed for 3 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. custompurified by column chromatography (methanol/ethyl acetate 20-30%)

Sources & evidence

ORD record
ord-ae9c292cbcdf4e6eadfdbac39a5cee9b
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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