Bromide ion → HCID 23627744, Verbindung
Reaktionsgleichung
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:38][C:39]([NH2:41])=[O:40].[Br-]>C1COCC1>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[CH2:38][C:39]([NH2:41])=[O:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
A solution of the bishydrochloride salt of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (110 mg, 0.25 mmol) in THF (2 mL) at room temperature was treated with diisopropylethylamine (165 μL, 1.0 mmol) followed by 2-bromoacetamide (42 mg, 0.3 mmol). The reaction mixture was heated at 50° C. for 8 h and an additional amount of bromide (42 mg, 0.3 mmol) then added. The reaction mixture was then stirred for an additional 16 h at room temperature and evaporated. The crude reaction was then partitioned between EtOAc (3 mL) and a saturated aqueous NaHCO3 solution (3 mL). The organic phase was isolated and further washed with an additional portion of a saturated aqueous NaHCO3 solution (3 mL) and brine (2×3 mL).
Aufarbeitung
- customevaporated
- customThe crude reaction
- customwas then partitioned between EtOAc (3 mL)
- customThe organic phase was isolated
- washfurther washed with an additional portion of a saturated aqueous NaHCO3 solution (3 mL) and brine (2×3 mL)
Quellen und Nachweise
- ORD-Eintrag
- ord-0b82a7b66e454e84ad26c5a1854d51e6
- Quelldatensatz
- uspto-grants-2010_11
- Patentnummer
- US07829713B2
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