Triethylamine → HCID 21993692, compound

HRID 1978504Notes

Reaction equation

HRID 1978504 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][S:10]/[CH:11]=[CH:12]/[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)[CH2:5][CH2:4]1.Br[CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(O)C>[C:29]1([CH2:28][CH2:27][CH2:26][N:3]2[CH2:8][CH2:7][CH:6]([CH2:9][S:10]/[CH:11]=[CH:12]/[C: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)[CH:14]=3)[CH2:5][CH2:4]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzeneHCID 516892Sodium BicarbonateHCID 21993754HCID 21993754, compound

Product 1

HCID 21993692HCID 21993692, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.314 g (0.780 mM) of (E)-4-[2-(piperidin-4-ylmethylthio)vinyl]-5-thia-1,8b-diazaacenaphthylene dihydrochloride, 0.19 g (0.94 mM) of 1-bromo-3-phenylpropane, and 0.38 ml (2.73 mM) of triethylamine in 20 ml of ethanol was refluxed for 1 day. This reaction mixture was poured in aqueous solution of sodium hydrogen carbonate and extracted with 2 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 4/1) to provide the title compound.

Workup

  1. extractionextracted with 2 portions of ethyl acetate
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 4/1)

Sources & evidence

ORD record
ord-3f8b6ff0b5bf4ddd934c74254061fb38
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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