1,2,3,4-Tetrahydroisoquinoline → Benzamide, N-(1,2,3,4-tetrahydro-2-methylisoquinolin-8-yl)-3,4,5-trimethoxy-

HRID 2397935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2397935
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[N+](C1C=CC=C2C=1C=[N+](C)C=C2)([O-])=O.C(=O)(O)[O-].[K+].[CH3:43][O:44][C:45]1[CH:46]=[C:47]([CH:51]=[C:52]([O:56][CH3:57])[C:53]=1[O:54][CH3:55])[C:48](Cl)=[O:49].C1C2C(=CC=CC=2)CCN1>C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:57][O:56][C:52]1[CH:51]=[C:47]([CH:46]=[C:45]([O:44][CH3:43])[C:53]=1[O:54][CH3:55])[C:48]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)=[O:49]

Komponenten

8

Edukt 5

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516893Potassium BicarbonateHCID 135299172-Methyl-1,2,3,4-tetrahydroisoquinolin-8-amineHCID 214367508-Nitro-2-methyl-isoquinolinium p-toluenesulfonate

Produkt 1

HCID 216590Benzamide, N-(1,2,3,4-tetrahydro-2-methylisoquinolin-8-yl)-3,4,5-trimethoxy-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

8-Amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (2 g) prepared from 8-nitro-2-methyl-isoquinolinium p-toluenesulfonate as described for the 5-nitro isomer in Example 4 was dissolved in dry benzene (100 ml) and 0.5 g of dry potassium bicarbonate was added. A 0.1 mole excess of 3,4,5-trimethoxybenzoyl chloride was dissolved in dry benzene (50 ml) and this solution was added to the solution of the tetrahydroisoquinoline. The solutions clouded on mixing and were then refluxed for 12 hours. After refluxing, the benzene was removed in vacuo leaving a viscous, yellow oil. This was suspended in 10% sodium carbonate solution to remove excess acid chloride. The insoluble oil was extracted from the aqueous sodium carbonate with chloroform which was dried over anhydrous magnesium sulfate. The chloroform was distilled off to leave a viscous, yellow oil. This was washed with ether and a white solid (3 g) formed. This was recrystallized from ethanol-water to yield the desired product as white felted needles, m.p. 177°-178.3° C.

Aufarbeitung

  1. additionon mixing
  2. temperaturewere then refluxed for 12 hours
  3. temperatureAfter refluxing
  4. customthe benzene was removed in vacuo
  5. customleaving a viscous, yellow oil
  6. customto remove excess acid chloride
  7. extractionThe insoluble oil was extracted from the aqueous sodium carbonate with chloroform which
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. distillationThe chloroform was distilled off
  10. customto leave a viscous, yellow oil
  11. washThis was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-9e6f7294473b4c09a93f29b220709064
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04022900

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