Water → (1S)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine

HRID 2056766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2056766
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:10]=[CH:11][C:12]3[C@H:17]([CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][N:23]([C:26]5[C:35]6[C:30](=[CH:31][C:32]([F:36])=[CH:33][CH:34]=6)[CH:29]=[CH:28][CH:27]=5)[CH2:22][C@H:21]4[CH3:37])[O:16][CH2:15][CH2:14][C:13]=3[CH:38]=2)C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO.O>CO>[F:36][C:32]1[CH:31]=[C:30]2[C:35](=[CH:34][CH:33]=1)[C:26]([N:23]1[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][C@H:17]3[C:12]4[CH:11]=[CH:10][C:9]([NH2:8])=[CH:38][C:13]=4[CH2:14][CH2:15][O:16]3)[C@H:21]([CH3:37])[CH2:22]1)=[CH:27][CH:28]=[CH:29]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86596019(1S)-N-(diphenylmethylene)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine

Produkt 1

HCID 69307771(1S)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (1S)-N-(diphenylmethylene)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]-ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine (1.46 g, 2.5 mmol) in methanol (25 mL) was added sodium acetate (0.28 g, 2.65 mmol) and hydroxylamine hydrochloride (0.194 g, 2.8 mmol), and the mixture stirred at room temperature under nitrogen for 18 h. Water was added and extracted with dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluting with methanol/ethyl acetate (0:100 to 15:85), to yield (1S)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine. M+H=420.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography on silica
  6. washeluting with methanol/ethyl acetate (0:100 to 15:85)

Quellen und Nachweise

ORD-Eintrag
ord-01e32e5160f64d4d8926680f1601644f
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335660B2

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