Sodium Iodide → 3-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

HRID 1173834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173834
[Cl:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]1=[O:19].Cl.Br[CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>>[ClH:1].[Cl:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21]([O:24][CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])=[CH:20][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:9]1=[O:19]

Komponenten

5

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 117103063-(3-Chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-oneHCID 12440776(3-Bromo-propyl)-dimethyl-amine hydrochloride

Produkt 1

HCID 117128103-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

Versuchsvorschrift

Using the procedure to synthesize Example 12 and using reagents 3-(3-chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (150 mg, 0.412 mmol), (3-bromo-propyl)-dimethyl-amine hydrochloride (167 mg, 0.824 mmol), sodium iodide (62 mg, 0.412 mmol), and cesium carbonate (1.07 g, 3.30 mmol) afford the freebase of the title compound. Dissolve freebase in dichloromethane (5 mL) and add HCl in ether (2M, 0.4 mL), concentrate to give title compound (105 mg, 52%) as a yellow solid: Mass spectrum (apci) m/z=449.3 (M+H).

Aufarbeitung

  1. customto synthesize Example 12

Quellen und Nachweise

ORD-Eintrag
ord-6dd880a8ec774983a6223b7864b974f6
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834194B2

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