Triethylamine → 7-(3-Cyanobenzamido)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235115Notes

Reaction equation

HRID 235115 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=[O:32])#[N:27]>C(#N)C>[C:26]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)=[O:32])#[N:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 223693767-(3-Cyanobenzamido)-1-(4-methyl-1-piperazinyl)-naphthaleneYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title product was prepared following the procedure of example 3 from 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.213 g, 0.883 mmol) and triethylamine (0.258 mL, 1.94 mmol) and 3-cyanobenzoyl chloride (0.322 g, 1.94 mmol) in acetonitrile (10 mL) with stirring at reflux for 2 hours and then at room temperature overnight. The mixture was concentrated and the residue was taken up in methylene chloride. This organic solution was washed with 0.5N sodium hydroxide, dried over calcium sulfate and concentrated. The product was isolated by silica gel flash chromatography and recrystallization from isopropyl alcohol to yield 0.184 g of (60%) of the title compound: mp 220°-222° C. Analysis calculated for C23H22N4O: C, 74.57; H, 5.99; N, 15.12. Found: C, 74.42; H, 5.78; N, 14.96.

Workup

  1. customThe title product was prepared
  2. temperatureat reflux for 2 hours
  3. customat room temperature
  4. customovernight
  5. concentrationThe mixture was concentrated
  6. washThis organic solution was washed with 0.5N sodium hydroxide
  7. dry with materialdried over calcium sulfate
  8. concentrationconcentrated
  9. customThe product was isolated by silica gel flash chromatography and recrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-d17dbf537ab94c9fbc1bc72d2628404f
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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