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
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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
SN - 1074-1542
VL - 34
SP - 239
EP - 244
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
IS - 4
ER -