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

HRID 35229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 35229
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bf0a2d4d017a45a3a5409ec7ef446b4b
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766131

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