Triethylamine → HCID 23333636, compound

HRID 904203Notes

Reaction equation

HRID 904203 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8](Cl)[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:5]=2[CH:4]=1)#[N:2].C(N(CC)CC)C.[H][H]>O1CCOCC1.[C].[Pd]>[C:1]([C:3]1[CH:19]=[CH:18][C:6]2[NH:7][CH2:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23333602HCID 23333602, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23333636HCID 23333636, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The resulting 2-cyano-6-chloro-11-oxodibenz[b,e]azepine (17.4 g) and triethylamine (9 g) were dissolved in dioxane (840 ml), and the solution was catalytically hydrogenated for 17 hours at room temperature at a hydrogen pressure of 4 kg/cm2 with 10% palladium-carbon powder (2 g) as a catalyst. After the hydrogenation, the catalyst was filtered off, and the filtrate was concentrated at reduced pressure. The concentrate was purified by silica gel chromatography, and recrystallized from acetone to obtain 5,6-dihydro-2-cyano-11-oxodibenz[b,e]azepine (7.06 g).

Workup

  1. filtrationAfter the hydrogenation, the catalyst was filtered off
  2. concentrationthe filtrate was concentrated at reduced pressure
  3. customThe concentrate was purified by silica gel chromatography
  4. customrecrystallized from acetone

Sources & evidence

ORD record
ord-349da8ed52204056bba1caad2a9e744d
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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