Diisopropylethylamine → N-[(1-(2-Methanesulphonamidoethyl)-4-piperidyl)methyl] 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

HRID 609600

Reaktionsgleichung

Reaktionsgleichung von HRID 609600
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]3[CH2:20][CH2:21][CH2:22][O:23][C:12]=23)=[O:10])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Br[CH2:34][CH2:35][NH:36][S:37]([CH3:40])(=[O:39])=[O:38]>C(#N)C.C(Cl)(Cl)Cl>[CH3:40][S:37]([NH:36][CH2:35][CH2:34][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]3[CH2:20][CH2:21][CH2:22][O:23][C:12]=23)=[O:10])[CH2:3][CH2:2]1)(=[O:39])=[O:38]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 285330N-(2-bromoethyl)methanesulfonamideHCID 9839803N-(4-Piperidylmethyl) 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

Produkt 1

HCID 19599423N-[(1-(2-Methanesulphonamidoethyl)-4-piperidyl)methyl] 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamideAusbeute 11,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred solution of N-(4-piperidylmethyl) 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxarnide (E21, 220 mg, 0.70 mmole) in acetonitrile (8 ml) was treated with diisopropylethylamine (0.24 ml, 1.4 mmole) and N-(2-bromoethyl)methanesulphonamide (D14, 160 mg, 0.77 mmole) and the mixture heated under reflux for 2.5 h. The reaction mixture was concentrated in vacuo and the residue chromatographed on silica gel eluting with dichloromethane/methanol/0.88 ammonia solution (200:10:1). The colourless oil obtained was dissolved in chloroform (30 ml) and washed with water (2×20 ml), then dried (Na2SO4) and concentrated in vacuo. The residue was passed through a short plug of basic alumina eluting with ethyl acetate to afford the title compound as a colourless oil (34 mg, 11%). This was converted to its oxalate salt and crystallised from acetone to give a white solid mp 80-85° C.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue chromatographed on silica gel eluting with dichloromethane/methanol/0.88 ammonia solution (200:10:1)
  5. customThe colourless oil obtained
  6. washwashed with water (2×20 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5711a6500e6e49b0bc2937a1673f499b
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998409

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