Triethylamine → HCID 70246921, compound

HRID 1978507Notes

Reaction equation

HRID 1978507 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][S:11](/[CH:14]=[CH:15]/[C:16]2[S:26][C:25]3[N:27]4[C:18](=[CH:19][N:20]=[C:21]4[CH:22]=[CH:23][CH:24]=3)[CH:17]=2)(=[O:13])=[O:12])[CH2:5][CH2:4]1.Br[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(O)C>[C:32]1([CH2:31][CH2:30][CH2:29][N:3]2[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][S:11](/[CH:14]=[CH:15]/[C:16]3[S:26][C:25]4[N:27]5[C:18](=[CH:19][N:20]=[C:21]5[CH:22]=[CH:23][CH:24]=4)[CH:17]=3)(=[O:13])=[O:12])[CH2:5][CH2:4]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzeneHCID 516892Sodium BicarbonateHCID 21993894HCID 21993894, compound

Product 1

HCID 70246921HCID 70246921, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.285 g (0.634 mM) of (E)-N-(piperidin-4-ylmethyl)-2-(5-thia-1,8b-diazaacenaphthylen-4-yl)vinylsulfonamide dihydrochloride, 0.15 g (0.76 mM) of 1-bromo-3-phenylpropane, and 0.31 ml (2.22 mM) of triethylamine in 20 ml of ethanol was refluxed for 1 day. This reaction mixture was then poured in aqueous solution of sodium hydrogen carbonate and extracted with 2 portions of ethyl acetate. The organic layers were combined 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) 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)

Sources & evidence

ORD record
ord-e03acf8758bd45f19d15a5753ff59b33
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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