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

HRID 622125

反応式

HRID 622125 の反応式
[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

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 3776Isopropanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-92b25b7f9dfd4d2bb4eea1a7d0574cb1
出典データセット
uspto-grants-1988_09
特許番号
US04769369

関連ノート

読み込み中…