Hydrochloric Acid → 3-(4-Hydroxybutyl)-1H-indole-5-carbonitrile

HRID 628790

Reaktionsgleichung

Reaktionsgleichung von HRID 628790
[CH:1]1[C:6]([C:7]#[N:8])=[CH:5][C:4]2[C:9]([CH2:12][CH2:13][CH2:14][CH2:15]N3CCN(C4C=CC5OC(C(N)=O)=CC=5C=4)CC3)=[CH:10][NH:11][C:3]=2[CH:2]=1.ClCCCC(C1C2C(=CC=C(C#N)C=2)NC=1)=[O:39].[BH4-].[Na+].Cl>C(O)(C)C>[OH:39][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[C:4]2[C:3](=[CH:2][CH:1]=[C:6]([C:7]#[N:8])[CH:5]=2)[NH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 6918314VilazodoneHCID 102205283-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

Produkt 1

HCID 121509853-(4-Hydroxybutyl)-1H-indole-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

As per the process described in CN'932 publication, vilazodone is prepared by reacting 3-(4-chlorobutyryl)-1H-indole-5-carbonitrile with sodium borohydride in isopropanol at reflux temperature, followed by treating the reaction mass with dilute hydrochloric acid and subsequent workup and then subjecting to column chromatography purifications to produce 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile. The hydroxylbutyl intermediate obtained is then subjected to sulfonylation using a sulfonylating agent selected from p-toluenesulfonyl chloride, benzenesulfonyl chloride, methanesulfonyl chloride and trifluoromethanesulfonyl chloride to produce corresponding sulfonylated intermediate, which is then condensed with 5-(1-piperazinyl)benzofuran-2-carboxamide in acetonitrile to produce vilazodone.

Aufarbeitung

  1. customis prepared
  2. temperatureat reflux temperature

Quellen und Nachweise

ORD-Eintrag
ord-94ad5614d6ce4816a24f02076f9a69d9
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315456B2

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