2-(1-Methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one: Acid-catalyzed isomerization of the Z isomer to the E isomer

Vijayakumar N. Sonar; Sean Parkin; Peter A. Crooks

doi:10.1023/B:JOCC.0000022421.28337.de

2-(1-Methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one: Acid-catalyzed isomerization of the Z isomer to the E isomer

Vijayakumar N. Sonar, Sean Parkin, Peter A. Crooks

Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

Crystals of (Z)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one (I) were obtained from a condensation reaction of 1-methyl-1H-indole-3-carboxaldehyde with 1-aza-bicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The isomeric (E)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one hydrochloride (II) was obtained by treating a methanolic solution of I with a 1M solution of hydrogen chloride diethyl ether, followed by crystallization of resultant product from methanol. Crystal data: I, is monoclinic, P2₁, a = 5.7440(10), b = 11.102(2), c = 10.708(2) Å, β = 91.751(10)°, and V = 682.5(2) Å³ with Z = 2, for D_cal = 1.296 mg/m³ and II, is monoclinic, P2₁/c, a = 8.8510(2), b = 17.4990(5), c = 20.4300(5) Å, β = 101.3620(12)°, V = 3102.26(14) with Z = 8, for D_cal = 1.316 mg/m³.

Original language	English
Pages (from-to)	239-244
Number of pages	6
Journal	Journal of Chemical Crystallography
Volume	34
Issue number	4
DOIs	https://doi.org/10.1023/B:JOCC.0000022421.28337.de
State	Published - Apr 2004

Keywords

Heterocycle
Indole
Quinuclidinone
Single crystal x-ray structure
Synthesis

ASJC Scopus subject areas

Chemistry (all)
Condensed Matter Physics

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@article{55b971ef6a1b4529abdc522131683438,

title = "2-(1-Methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one: Acid-catalyzed isomerization of the Z isomer to the E isomer",

abstract = "Crystals of (Z)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one (I) were obtained from a condensation reaction of 1-methyl-1H-indole-3-carboxaldehyde with 1-aza-bicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The isomeric (E)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one hydrochloride (II) was obtained by treating a methanolic solution of I with a 1M solution of hydrogen chloride diethyl ether, followed by crystallization of resultant product from methanol. Crystal data: I, is monoclinic, P21, a = 5.7440(10), b = 11.102(2), c = 10.708(2) {\AA}, β = 91.751(10)°, and V = 682.5(2) {\AA}3 with Z = 2, for Dcal = 1.296 mg/m3 and II, is monoclinic, P21/c, a = 8.8510(2), b = 17.4990(5), c = 20.4300(5) {\AA}, β = 101.3620(12)°, V = 3102.26(14) with Z = 8, for Dcal = 1.316 mg/m3.",

keywords = "Heterocycle, Indole, Quinuclidinone, Single crystal x-ray structure, Synthesis",

author = "Sonar, {Vijayakumar N.} and Sean Parkin and Crooks, {Peter A.}",

year = "2004",

month = apr,

doi = "10.1023/B:JOCC.0000022421.28337.de",

language = "English",

volume = "34",

pages = "239--244",

number = "4",

}

TY - JOUR

T1 - 2-(1-Methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one

T2 - Acid-catalyzed isomerization of the Z isomer to the E isomer

AU - Sonar, Vijayakumar N.

AU - Parkin, Sean

AU - Crooks, Peter A.

PY - 2004/4

Y1 - 2004/4

N2 - Crystals of (Z)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one (I) were obtained from a condensation reaction of 1-methyl-1H-indole-3-carboxaldehyde with 1-aza-bicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The isomeric (E)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one hydrochloride (II) was obtained by treating a methanolic solution of I with a 1M solution of hydrogen chloride diethyl ether, followed by crystallization of resultant product from methanol. Crystal data: I, is monoclinic, P21, a = 5.7440(10), b = 11.102(2), c = 10.708(2) Å, β = 91.751(10)°, and V = 682.5(2) Å3 with Z = 2, for Dcal = 1.296 mg/m3 and II, is monoclinic, P21/c, a = 8.8510(2), b = 17.4990(5), c = 20.4300(5) Å, β = 101.3620(12)°, V = 3102.26(14) with Z = 8, for Dcal = 1.316 mg/m3.

AB - Crystals of (Z)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one (I) were obtained from a condensation reaction of 1-methyl-1H-indole-3-carboxaldehyde with 1-aza-bicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The isomeric (E)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one hydrochloride (II) was obtained by treating a methanolic solution of I with a 1M solution of hydrogen chloride diethyl ether, followed by crystallization of resultant product from methanol. Crystal data: I, is monoclinic, P21, a = 5.7440(10), b = 11.102(2), c = 10.708(2) Å, β = 91.751(10)°, and V = 682.5(2) Å3 with Z = 2, for Dcal = 1.296 mg/m3 and II, is monoclinic, P21/c, a = 8.8510(2), b = 17.4990(5), c = 20.4300(5) Å, β = 101.3620(12)°, V = 3102.26(14) with Z = 8, for Dcal = 1.316 mg/m3.

KW - Heterocycle

KW - Indole

KW - Quinuclidinone

KW - Single crystal x-ray structure

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=3543138957&partnerID=8YFLogxK

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U2 - 10.1023/B:JOCC.0000022421.28337.de

DO - 10.1023/B:JOCC.0000022421.28337.de

M3 - Article

AN - SCOPUS:3543138957

VL - 34

SP - 239

EP - 244

IS - 4

ER -

2-(1-Methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one: Acid-catalyzed isomerization of the Z isomer to the E isomer

Abstract

Keywords

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