Triethylamine → HCID 70247622, compound

HRID 1978493Notes

Reaction equation

HRID 1978493 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([C:9](=[O:24])/[CH:10]=[CH:11]/[C:12]2[S:22][C:21]3[N:23]4[C:14](=[CH:15][N:16]=[C:17]4[CH:18]=[CH:19][CH:20]=3)[CH:13]=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(#N)C>[C:29]1([CH2:28][CH2:27][CH2:26][N:3]2[CH2:8][CH2:7][CH:6]([C:9](=[O:24])/[CH:10]=[CH:11]/[C:12]3[S:22][C:21]4[N:23]5[C:14](=[CH:15][N:16]=[C:17]5[CH:18]=[CH:19][CH:20]=4)[CH:13]=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 70243410HCID 70243410, compound

Product 1

HCID 70247622HCID 70247622, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.675 g (1.756 mM) of (E)-1-(piperidin-4-yl)-3-(5-thia-1,8b-diazaacenaphthylen-4-yl)propen-1-one dihydrochloride, 0.52 g (2.63 mM) of 1-bromo-3-phenylpropane, and 0.86 ml (6.15 mM) of triethylamine in 30 ml of acetonitrile, and the mixture was refluxed for 1 day. This reaction mixture was 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˜ethyl acetate/methanol: 4/1) 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˜ethyl acetate/methanol: 4/1)

Sources & evidence

ORD record
ord-c2a3a90d5c934b4aa9e5b42ede7b5e60
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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