Ethyl isocyanate → (rac)-1-(4-(4-Cyanophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)-3-ethylurea

HRID 714065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714065
[NH2:1][CH:2]1[C:11]2[CH:10]=[N:9][CH:8]=[C:7]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21].CCN(CC)CC.OP([O-])(O)=O.[K+]>C(Cl)Cl.CO>[C:16]([C:15]1[CH:14]=[CH:13][C:12]([C:7]2[C:6]3[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][C:23]([NH:22][CH2:20][CH3:21])=[O:24])[C:11]=3[CH:10]=[N:9][CH:8]=2)=[CH:19][CH:18]=1)#[N:17]

Komponenten

7

Edukt 4

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 516951Monobasic potassium phosphateHCID 718113604-(8-Amino-5,6,7,8-tetrahydro-4-isoquinolinyl)benzonitrile

Produkt 1

HCID 89846368(rac)-1-(4-(4-Cyanophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)-3-ethylureaAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A cooled (0° C.) solution of (rac)-4-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile (example 1) (62.3 mg, 250 μmol) in CH2Cl2 (5 mL) was treated with ethyl isocyanate (51.6 μL, 625 μmol) in CH2Cl2 (0.6 mL) and Et3N (69.7 μL, 500 μmol). After ½ h the solution was stirred at room temperature for 1 h and treated with MeOH (0.2 mL). The reaction mixture was poured on aq. 10% KH2PO4 solution followed by extraction with AcOEt (3×). The organic phases were washed once with aq. sat. NaCl solution. The combined organic phases were dried (Na2SO4), filtered and purified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 3%)). Precipitation from CH2Cl2 with n-pentane gave the title compound (64 mg, 80%) as off-white powder. MS: 321.2 (M+H+).

Aufarbeitung

  1. extractionfollowed by extraction with AcOEt (3×)
  2. washThe organic phases were washed once with aq. sat. NaCl solution
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. custompurified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 3%))
  6. customPrecipitation from CH2Cl2 with n-pentane

Quellen und Nachweise

ORD-Eintrag
ord-1b7025e9576d4572ba0f7ba2cf6b93c0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187429B2

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