Phenethylamine → 2-(2-Chloropropionyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 844953

반응식

HRID 844953 반응식
C(N)CC1C=CC=CC=1.C(Cl)(=O)C1C=CC=CC=1.[C:19]1([CH:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:47][CH:48]([CH3:52])[C:49](Cl)=[O:50]>O.C(Cl)Cl>[Cl:47][CH:48]([CH3:52])[C:49]([N:26]1[CH2:27][CH2:28][C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:50]

참가 물질

9

반응물 6

HCID 1001PhenethylamineHCID 7412Benzoyl chlorideHCID 8405IsoquinolineHCID 14798Sodium HydroxideHCID 1001371,2,3,4-Tetrahydro-1-phenylisoquinolineHCID 1110192-Chloropropionyl chloride

생성물 1

HCID 201330512-(2-Chloropropionyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

By procedures described in Example 1 (Method A), phenethylamine and benzoyl chloride were converted to 1-phenyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 5 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1 ml 2-chloropropionyl chloride was added dropwise to the mixture. The mixture was stirred for 10 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (170° C. @ 0.1 mm Hg) to provide 2.3 g of a viscous yellow oil product having the elemental analysis reported in Table I.

후처리

  1. stirringThe mixture was stirred for 10 minutes
  2. extractionThe organic extract
  3. dry with materialwas dried with magnesium sulfate
  4. distillationsubjected to Kugelrohr distillation (170° C. @ 0.1 mm Hg)

출처 및 근거

ORD 기록
ord-8104b3380a254884baca8cfa441d0576
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04755218

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