4-Methoxystyrene → Trans-6-[2-(4-methoxyphenyl)ethenyl]-2-(3-piperidinopropyl)phthalazin-1(2H)-one hydrobromide

HRID 622125노트

반응식

HRID 622125 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[N:6]=[CH:5]2.Cl.ClCCCN1CCCCC1.Cl.C(N(C(C)C)CCCl)(C)C.[CH3:44][O:45][C:46]1[CH:53]=[CH:52][C:49]([CH:50]=[CH2:51])=[CH:48][CH:47]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(O)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C.CS(C)=O>[BrH:1].[CH3:44][O:45][C:46]1[CH:53]=[CH:52][C:49](/[CH:50]=[CH:51]/[C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[N:6]=[CH:5]3)=[CH:48][CH:47]=1

참가 물질

10

반응물 5

HCID 125074-MethoxystyreneHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 80271Tri-o-tolylphosphineHCID 212933476-Bromo-2-(3-piperidinopropyl)phthalazin-1(2H)-one

생성물 1

HCID 21293325Trans-6-[2-(4-methoxyphenyl)ethenyl]-2-(3-piperidinopropyl)phthalazin-1(2H)-one hydrobromide

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 679Dimethyl Sulfoxide용매HCID 3776Isopropanol용매HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

6-Bromo-2-(3-piperidinopropyl)phthalazin-1(2H)-one (7.2 gm, 0.018 mole) (prepared as in Example I, except that 1-(3-chloropropyl)piperidine hydrochloride was substituted for the 2-(diisopropylamino)ethyl chloride hydrochloride) was stirred into 10 ml DMSO plus 10 ml acetonitrile. To the resulting mixture was added 2.8 gm 4-methoxystyrene (0.021 mole), 0.1 gm tri(o-tolyl)phosphine, and 0.02 gm palladium acetate. The reaction mixture was stirred at reflux (95°-100° C.) for 24 hours. Allowed to cool to about 60° C. and diluted with 40 ml of isopropanol. Stirred for an hour, filtered, washed to colorless washings with isopropanol and dried. The product weighed 8.6 gm. After recrystallization from 50 ml methoxyethanol the product weighed 6.4 gm and melted at 248°-250° C.

후처리

  1. temperatureat reflux (95°-100° C.) for 24 hours
  2. stirringStirred for an hour
  3. filtrationfiltered
  4. washwashed
  5. washwashings with isopropanol
  6. customdried
  7. customAfter recrystallization from 50 ml methoxyethanol the product

출처 및 근거

ORD 기록
ord-92b25b7f9dfd4d2bb4eea1a7d0574cb1
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04769369

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