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

HRID 235115노트

반응식

HRID 235115 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d17dbf537ab94c9fbc1bc72d2628404f
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597826

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