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Process for producing 3-Aminocyclohex-2-en-1-ylidene Compounds

IP.com Disclosure Number: IPCOM000225139D
Publication Date: 2013-Jan-25

Publishing Venue

The IP.com Prior Art Database

Abstract

3-Aminocyclohex-2-en-1-ylidene derivatives represent a class of particularly efficient UV-A absorbers. Their synthesis is briefly reviewed. A convenient synthesis route is described comprising the condensation reaction of an 3-aminocyclohex-2-en-1-one compound with an methylene active compound. Different separation and purification techniques are also described.

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Process for producing 3-Aminocyclohex-2-en-1-ylidene Compounds

Keywords: 3-aminocyclohex-2-en-1-ylidene derivatives; UV stabilizers; condensation; purification; adsorbents.

Described is a process for producing 3-amino-2-cyclohexan-1-ylidene derivatives represented by the following formula (1), the process including reacting an 3-aminocyclohex- 2-en-1-one compound represented by the following formula (2) with a methylene active compound represented by the following formula (3):


(1)

N

R 4 R 3 R 2 R 1

     R 6 R 5

R3 R4

N O


(2)

R5 R6


(3) R1

  R2 H H

wherein

R1 and R2 independently of each other are CN; -COOR7; -CONHR7; -COR7; or -SO2R7; or -CONR7R8;; or

R1 and R2 together form a five or six membered ring;

R3 and R4 independently of each other are hydrogen; C1-C22 alkyl; C2-C22 alkenyl, C2-C22 alkinyl, C3-C12 cycloalkyl, C3-C12 cycloalkenyl, C7-C20 aralkyl, C1-C20 heteroalkyl, C3-C12 cycloheteroalkyl, C5-C11 heteroaralkyl, C6-C20aryl or C4-C9 heteroaryl; or

R3 and R4 together form a five or six membered ring;

R5 and R6 independently of each other are hydrogen; C1-C22 alkyl; C2-C22 alkenyl; or

R5 and R6 together form a five or six membered ring;

R7 and R8 independently of each other are hydrogen, C1-C22 alkyl, C2-C22 alkenyl, C2-C22 alkinyl, C3-C12 cycloalkyl, C3-C12 cycloalkenyl, C7-C20 aralkyl, C1-C20 heteroalkyl, C3-C12 cycloheteroalkyl, C5-C11 heteroaralkyl, C6-C20 aryl or C4-C9 heteroaryl; or

R7 and R8 together form a five or six membered ring.

C1-C30alkyl are straight chain or branched radicals like methyl, ethyl, n-propyl, isopropyl, n- butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, hexyl, 2-ethylhexyl, heptyl, octyl,


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isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, undecyl, eicosyl, tetracosyl, pentacosyl, heptacosyl, octacosyl or triacontyl.

C1-C30alkoxy are straight chain or branched radicals like methoxy, ethoxy, n-propoxy, iso- propoxy, n-butyloxy, sec-butyloxy, tert-butyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, 2-ethylhexyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy, undecyloxy eicosyloxy tetracosyloxy, pentacosyloxy, heptacosyloxy, octacosyloxy or triacontyloxy.

C2-C30alkenyl are straight chain or branched radicals like allyl, methallyl, isopropenyl, 2-bu- tenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2- enyl, iso-dodecenyl, n-dodec-2-enyl, n-octadec-4-enyl, eicosenyl, tetracosenyl, pentacoensyl, heptacosenyl, octacosenyl or triacontenyl.

C3-C12cycloalkyl is for example cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl and preferably cyclohexyl.

Hetero-C3-C12aryl is preferably pyridinyl, pyrimidinyl, triazinyl, pyrrolyl, furanyl, thiophenyl or chinolinyl.

C6-C20aryl is for example naphthyl and preferably phenyl or biphenyl.

Each alkyl can be linear or branched. Each alkyl or cycloalkyl can be saturated or unsaturated.

Each...