KR970042483A - Method for preparing arylpropylamine derivative - Google Patents

Method for preparing arylpropylamine derivative Download PDF

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Publication number
KR970042483A
KR970042483A KR1019950046411A KR19950046411A KR970042483A KR 970042483 A KR970042483 A KR 970042483A KR 1019950046411 A KR1019950046411 A KR 1019950046411A KR 19950046411 A KR19950046411 A KR 19950046411A KR 970042483 A KR970042483 A KR 970042483A
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South Korea
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general formula
group
compound
hydrogen
substituted phenyl
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KR1019950046411A
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Korean (ko)
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KR100187396B1 (en
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박노상
정영식
성철민
최진일
최승원
이종철
최연주
이광숙
황경란
한만소
김란희
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강박광
재단법인 한국화학연구소
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains

Abstract

본 발명은 소염 및 진통작용이 우수한 페닐아세테이트 유도체의 중간체로서 유용한 하기 일반식(Ⅰ)로 표시되는 아릴프로필아민 유도체를 아릴할라이드 화합물을 원료로하여 제조하는 방법에 관한 것이다.The present invention relates to a method for producing an arylpropylamine derivative represented by the following general formula (I), which is useful as an intermediate of phenylacetate derivative having excellent anti-inflammatory and analgesic activity, using an aryl halide compound as a raw material.

(Ⅰ) (Ⅰ)

상기식에서 R1, R2는 각각 수소, 할로겐, 니트로기, 치환된 페닐기, R3, OR3, SR3또는 NR3R4로서, 이때 R3, R4는 각각 수소, 탄소수 1 내지 8의 알킬기, 고리알킬기 또는 치환된 페닐기 이고, Z는 서로 같거나 다를 수 있으며, 수소, 할로겐, 니트로기, 치환된 페닐기, R3, OR3, SR3또는 NR3R4로서, 이때 R3, R4는 위에서 정의한 바와 같고, p는 0내지 5의 정수이다.Wherein R 1 , R 2 are each hydrogen, halogen, nitro group, substituted phenyl group, R 3 , OR 3 , SR 3 or NR 3 R 4 , wherein R 3 , R 4 are each hydrogen, having from 1 to 8 carbon atoms An alkyl group, a cyclic alkyl group or a substituted phenyl group, Z may be the same or different from each other, and hydrogen, halogen, nitro group, substituted phenyl group, R 3 , OR 3 , SR 3 or NR 3 R 4 , wherein R 3 , R 4 is as defined above and p is an integer from 0 to 5.

Description

아릴프로필아민 유도체의 제조방법Method for preparing arylpropylamine derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (9)

(가) 하기 일반식(Ⅱ)의 아릴할라이드와 하기 일반식(Ⅲ)의 올레핀유도체를 반응시킴으로써 하기 일반식(Ⅳ)의 화합물을 얻는 단계 (제1단계); (나) 상기 제 1단계에서 얻은 일반식(Ⅳ) 화합물의 이중 결합 환원시켜 하기 일반식(Ⅴ)의 화합물을 얻는 단계 (제 2단계); 및 (다) 상기 제 2단계에서 얻은 일반식(Ⅴ) 화합물을 환원시켜 하기 일반식(Ⅰ) 화합물을 얻는 단계 (제 3단계); 로 이루어지는 것을 특징으로 하는 하기 일반식(Ⅰ)의 아릴프로필아민 유도체의 제조방법.(A) obtaining the compound of the following general formula (IV) by reacting the aryl halide of the following general formula (II) with the olefin derivative of the following general formula (III) (first step); (B) obtaining a compound of the following general formula (V) by reducing the double bond of the compound of the general formula (IV) obtained in the first step (second step); And (c) reducing the compound of formula (V) obtained in the second step to obtain a compound of formula (I) (third step); A process for producing an arylpropylamine derivative of the general formula (I) below, which comprises: (식중, R1, R2는 각각 수소, 할로겐, 니트로기, 치환된 페닐기, R3, OR3, SR3또는 NR3R4로서, 이때 R3, R4는 각각 수소, 탄소수 1 내지 8의 알킬기, 고리알킬기 또는 치환된 페닐기 이고, Z는 서로 같거나 다를 수 있으며, 수소, 할로겐, 니트로기, 치환된 페닐기, R3, OR3, SR3또는 NR3R4로서, 이때 R3, R4는 위에서 정의한 바와 같고, p는 0내지 5의 정수이고, X는 C1, Br, I 또는 OSO2CF3이고, Y는 CN 또는 CONH2이다.)Wherein R 1 , R 2 are each hydrogen, halogen, nitro group, substituted phenyl group, R 3 , OR 3 , SR 3 or NR 3 R 4 , wherein R 3 , R 4 are each hydrogen, 1 to 8 carbon atoms Is an alkyl group, a cyclic alkyl group or a substituted phenyl group, Z may be the same as or different from each other, and hydrogen, halogen, nitro group, substituted phenyl group, R 3 , OR 3 , SR 3 or NR 3 R 4 , wherein R 3 , R 4 is as defined above, p is an integer from 0 to 5, X is C1, Br, I or OSO 2 CF 3 , and Y is CN or CONH 2. ) 제 1항에 있어서, Zp는 3-메틸 또는 3.4-디메틸이고, X는 Br 또는 I인 것을 특징으로 하는 방법.The method of claim 1, wherein Zp is 3-methyl or 3.4-dimethyl and X is Br or I. 제 1항 또는 제 2항에 있어서, 상기 제 1단계에서는 사용된 일반식(Ⅱ)의 아릴할라이드에 대해 몰비로 0.8 내지 1.5배의 염, 사용된 일반식 (Ⅱ)의 아릴할라이드에 대해 몰비로 0.01 내지 1%의 팔라디움 착콜 또는 팔라디움 2가염, 그리고 사용된 일반식 (Ⅱ)의 아릴할라이드에 대해 몰비로 0.1 내지 5%의 트리아릴포스핀이 반응시약으로서 사용되는 것을 특징으로 하는 방법.The method according to claim 1 or 2, wherein in the first step, the salt is 0.8 to 1.5 times the molar ratio of the aryl halide of the general formula (II), and the molar ratio of the aryl halide of the general formula (II) used. 0.01 to 1% palladium complex call or palladium divalent salt and 0.1 to 5% triarylphosphine in a molar ratio relative to the arylhalide of general formula (II) used are used as reaction reagents. 제 1항 또는 제 2항에 있어서, 상기 제 2단계에서는 환원제로서 H2/PtO2, H2/Pd, H2/Co 및 H2/Raney Ni로 이루어진 군에서 선택된 금속환원제가 사용되는 것을 특징으로 하는 방법.The metal reducing agent according to claim 1 or 2, wherein the metal reducing agent selected from the group consisting of H 2 / PtO 2 , H 2 / Pd, H 2 / Co, and H 2 / Raney Ni is used as the reducing agent. How to. 제 1항 또는 제 2항에 있어서, 상기 제 3단계에서는 환원제로서 LiAlH4, LiAlH(OR)3, AlH3, H2/PtO2, BH3, H2/Pd, H2/Co 및 H2/Raney Ni로 이루어진 군에서 선택된 금속환원제가 사용되는 것을 특징으로 하는 방법.The method according to claim 1 or 2, wherein in the third step, LiAlH 4 , LiAlH (OR) 3 , AlH 3 , H 2 / PtO 2 , BH 3 , H 2 / Pd, H 2 / Co, and H 2 as reducing agents. A metal reducing agent selected from the group consisting of / Raney Ni is used. (가) 하기 일반식(Ⅱ)의 아릴할라이드와 하기 일반식(Ⅲ)의 올레핀유도체를 반응시킴으로써 하기 일반식(Ⅳ)의 화합물을 얻는 단계 (제1단계); (나) 상기 제 1단계에서 얻은 일반식(Ⅳ) 화합물의 환원시켜 하기 일반식(Ⅰ)의 화합물을 얻는 단계 (제 2단계);로 이루어지는 것을 특징으로 하는 하기 일반식(Ⅰ)의 아릴프로필아민 유도체의 제조방법.(A) obtaining the compound of the following general formula (IV) by reacting the aryl halide of the following general formula (II) with the olefin derivative of the following general formula (III) (first step); (B) reducing the compound of the general formula (IV) obtained in the first step to obtain a compound of the general formula (I) (second step); arylpropyl of the general formula (I) Method for preparing an amine derivative. (식중, R1, R2는 각각 수소, 할로겐, 니트로기, 치환된 페닐기, R3, OR3, SR3또는 NR3R4로서, 이때 R3, R4는 각각 수소, 탄소수 1 내지 8의 알킬기, 고리알킬기 또는 치환된 페닐기 이고, Z는 서로 같거나 다를 수 있으며, 수소, 할로겐, 니트로기, 치환된 페닐기, R3, OR3, SR3또는 NR3R4로서, 이때 R3, R4는 위에서 정의한 바와 같고, p는 0내지 5의 정수이고, X는 C1, Br, I 또는 OSO2CF3이고, Y는 CN 또는 CONH2이다.)Wherein R 1 , R 2 are each hydrogen, halogen, nitro group, substituted phenyl group, R 3 , OR 3 , SR 3 or NR 3 R 4 , wherein R 3 , R 4 are each hydrogen, 1 to 8 carbon atoms Is an alkyl group, a cyclic alkyl group or a substituted phenyl group, Z may be the same as or different from each other, and hydrogen, halogen, nitro group, substituted phenyl group, R 3 , OR 3 , SR 3 or NR 3 R 4 , wherein R 3 , R 4 is as defined above, p is an integer from 0 to 5, X is C1, Br, I or OSO 2 CF 3 , and Y is CN or CONH 2. ) 제 6항에 있어서, Zp는 3-메틸 또는 3.4-디메틸이고, X는 Br 또는 I인 것을 특징으로 하는 방법.7. The method of claim 6, wherein Zp is 3-methyl or 3.4-dimethyl and X is Br or I. 제 6항 또는 제 7항에 있어서, 상기 제 1단계에서는 사용된 일반식(Ⅱ)의 아릴할라이드에 대해 몰비로 0.8 내지 1.5배의 염, 사용된 일반식 (Ⅱ)의 아릴할라이드에 대해 몰비로 0.01 내지 1%의 팔라디움 착콜 또는 팔라디움 2가염, 그리고 사용된 일반식 (Ⅱ)의 아릴할라이드에 대해 몰비로 0.1 내지 5%의 트리아릴포스핀이 반응시약으로서 사용되는 것을 특징으로 하는 방법.8. A salt according to claim 6 or 7, wherein in the first step, the salt is 0.8 to 1.5 times the molar ratio of the aryl halide of the general formula (II), and the molar ratio of the aryl halide of the general formula (II) used. 0.01 to 1% palladium complex call or palladium divalent salt and 0.1 to 5% triarylphosphine in a molar ratio relative to the arylhalide of general formula (II) used are used as reaction reagents. 제 6항 또는 제 7항에 있어서, 상기 제 2단계에서는 환원제로서 LiAlH4, LiAlH(OR)3, AlH3, H2/PtO2, BH3, H2/Pd, H2/Co 및 H2/Raney Ni로 이루어진 군에서 선택된 금속환원제가 사용되는 것을 특징으로 하는 방법.The method according to claim 6 or 7, wherein in the second step, LiAlH 4 , LiAlH (OR) 3 , AlH 3 , H 2 / PtO 2 , BH 3 , H 2 / Pd, H 2 / Co and H 2 as reducing agents. A metal reducing agent selected from the group consisting of / Raney Ni is used.
KR1019950046411A 1995-12-04 1995-12-04 Method for manufacturing arylpropilamine derivative KR100187396B1 (en)

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KR100187396B1 KR100187396B1 (en) 1999-05-15

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