Triethylamine → HCID 21993866, compound

HRID 1978497Notes

Reaction equation

HRID 1978497 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][C:11](=[O:26])/[CH:12]=[CH:13]/[C:14]2[S:24][C:23]3[N:25]4[C:16](=[CH:17][N:18]=[C:19]4[CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[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][CH2:10][C:11](=[O:26])/[CH:12]=[CH:13]/[C:14]3[S:24][C:23]4[N:25]5[C:16](=[CH:17][N:18]=[C:19]5[CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[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 21994007HCID 21994007, compound

Product 1

HCID 21993866HCID 21993866, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.362 g (0.878 mM) of (E)-5-(piperidin-4-yl]-1-(5-thia-1,8b-diazaacenaphthylen-4-yl)-1-penten-3-one dihydrochloride, 0.26 g (1.32 mM) of 1-bromo-3-phenylpropane, and 0.43 ml (3.07 mM) of triethylamine in 30 ml of ethanol was refluxed for 1 day. The reaction mixture was then poured in aqueous solution of sodium hydrogen carbonate and extracted with 3 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 : 9/1) to provide the title compound.

Workup

  1. extractionextracted with 3 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 : 9/1)

Sources & evidence

ORD record
ord-ed47692aa9154286a3e3d7b99ecec9dd
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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