Triethylamine → N-[3-(3-cyanophenyl)propyl]-4-cyanobenzamide

HRID 747751Notes

Reaction equation

HRID 747751 reaction equation
[H-].[Na+].[NH:3](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.Br[CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26].[C:30]([C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)#[N:31].C(N(CC)CC)C>CN(C=O)C.Cl.O1CCOCC1.C(OCC)(=O)C>[C:25]([C:24]1[CH:23]=[C:22]([CH2:21][CH2:20][CH2:19][NH:3][C:36](=[O:37])[C:35]2[CH:39]=[CH:40][C:32]([C:30]#[N:31])=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)#[N:26]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 801724-Cyanobenzoyl chlorideHCID 279800Di-tert-butyl IminodicarboxylateHCID 193772303-(3-Bromopropyl)benzonitrile

Product 1

HCID 68831035N-[3-(3-cyanophenyl)propyl]-4-cyanobenzamide

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

267 mg (7.23 mmol) of sodium hydride (65%) was dissolved in 8 ml of DMF in argon atmosphere. 1.43 g (6.57 mmol) of di-t-butyl iminodicarboxylate was added to the solution, and they were stirred at room temperature for 30 minutes. 1.47 g (6.57 mmol) of 3-(3-bromopropyl)benzonitrile was added to the resultant mixture. They were stirred at 45° C. for 3 hours. After the treatment with ethyl acetate as the extractant in an ordinary manner, an oily residue was obtained. This residue was dissolved in 4 N solution of hydrogen chloride in dioxane, and the solution was stirred at room temperature for 4 hours. The solvent was evaporated, and the oily residue was dissolved in 10 ml of dichloromethane. 1.63 g (9.86 mmol) of 4-cyanobenzoyl-chloride and 1.83 ml (13.4 mmol) of triethylamine were added to the solution, and they were stirred at room temperature for 5 hours. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. stirringThey were stirred at 45° C. for 3 hours
  2. stirringthe solution was stirred at room temperature for 4 hours
  3. customThe solvent was evaporated
  4. dissolutionthe oily residue was dissolved in 10 ml of dichloromethane
  5. stirringwere stirred at room temperature for 5 hours
  6. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-61ac637f63cd43e1a303d7d941246e85
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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