Triethylamine → HCID 21993869, compound

HRID 1978501Notes

Reaction equation

HRID 1978501 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][S:10](/[CH:13]=[CH:14]/[C:15]2[S:25][C:24]3[N:26]4[C:17](=[CH:18][N:19]=[C:20]4[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)(=[O:12])=[O:11])[CH2:5][CH2:4]1.Br[CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(O)C>[C:31]1([CH2:30][CH2:29][CH2:28][N:3]2[CH2:8][CH2:7][CH:6]([CH2:9][S:10](/[CH:13]=[CH:14]/[C:15]3[S:25][C:24]4[N:26]5[C:17](=[CH:18][N:19]=[C:20]5[CH:21]=[CH:22][CH:23]=4)[CH:16]=3)(=[O:12])=[O:11])[CH2:5][CH2:4]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzeneHCID 516892Sodium BicarbonateHCID 21993711HCID 21993711, compound

Product 1

HCID 21993869HCID 21993869, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.402 g (0.925 mM) of (E)-4-[2-(piperidin-4-ylmethanesulfonyl)vinyl]-5-thia-1,8b-diazaacenaphthylene dihydrochloride, 0.28 g (1.39 mM) of 1-bromo-3-phenylpropane, and 0.45 ml (3.24 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˜ethyl acetate/methanol : 9/1-1/1) 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˜ethyl acetate/methanol : 9/1-1/1)

Sources & evidence

ORD record
ord-06bbc610f67746e08a2f735cbf9800a6
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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