Pyridine → Diethylether hexane

HRID 1954781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1954781
[NH2:1][C@@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.N1C=CC=CC=1.[F:25][C:26]([F:37])([F:36])[C:27]([O:29][C:30](=O)[C:31](F)(F)F)=[O:28]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:27]([O:29][CH2:30][CH3:31])[CH3:26].[CH3:10][CH2:11][CH2:2][CH2:3][CH2:4][CH3:5].[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH2:3][C@H:2]([NH:1][C:27](=[O:28])[C:26]([F:37])([F:36])[F:25])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Produkt 2

HCID 21584099Diethylether hexaneAusbeute 104,4 %HCID 54128870HCID 54128870, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.49 mmol), pyridine (100 μL, 1.2 mmol) and 4-dimethylaminopyridine (20 mg, 0.16 mmol) in methylene chloride (10 mL) was added dropwise trifluoroacetic anhydride (72 μL, 0.51 mmol). After the addition the reaction was allowed to stir at ambient temperature for 1 h and was then washed with water. The methylene chloride phase was dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel column using ethyl acetate/methanol/concentrated ammonium hydroxide (96:4:0.5) as the eluent. This gave after crystallization from diethyl ether/hexane 41 mg (24% yield) of the title compound as white crystals: mp 158-159° C.; [α]21D +39° (c 0.25, chloroform); EIMS (70 eV) m/z (relative intensity) 341 (82, M+).

Aufarbeitung

  1. additionAfter the addition the reaction
  2. washwas then washed with water
  3. dry with materialThe methylene chloride phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified on a silica gel column
  7. customThis gave

Quellen und Nachweise

ORD-Eintrag
ord-d8deb3bae2014fd2aebf09ea7d6d9405
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124283

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