6,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline → N-(3-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

HRID 35229

반응식

HRID 35229 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH3:15])[NH:8][CH2:7][CH2:6]2.[N+:16]([C:19]1[CH:20]=[C:21]([CH2:25][C:26](O)=[O:27])[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[N+:16]([C:19]1[CH:20]=[C:21]([CH2:25][C:26]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]2[CH3:15])=[O:27])[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17]

참가 물질

5

반응물 3

HCID 103026,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineHCID 10868DicyclohexylcarbodiimideHCID 158763-Nitrophenylacetic acid

생성물 1

HCID 14230297N-(3-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline수율 64%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (20.0 g, 0.096 m) in methylene chloride (300 ml) under nitrogen at ambient temperature was added m-nitrophenylacetic acid (17.5 g, 0.096 m) and then portionwise dicyclohexylcarbodiimide (20.7 g, 0.1 m) and the mixture stirred for 3 hours. The precipitated solid was removed by filtration and the filtrate evaporated to an oily residue. This was treated with 100 ml methanol and 50 ml ether and the solid precipitate collected by filtration and washed with methanol and dried to give N-(3-nitrophenylacetyl)- 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline as a yellow solid, 22.0 g (64% yield), m.p. 120°-121°.

후처리

  1. customThe precipitated solid was removed by filtration
  2. customthe filtrate evaporated to an oily residue
  3. additionThis was treated with 100 ml methanol and 50 ml ether
  4. filtrationthe solid precipitate collected by filtration
  5. washwashed with methanol
  6. customdried

출처 및 근거

ORD 기록
ord-bf0a2d4d017a45a3a5409ec7ef446b4b
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766131

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