CN112979584A - 一种Mannich碱的制备方法 - Google Patents
一种Mannich碱的制备方法 Download PDFInfo
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- CN112979584A CN112979584A CN201911279155.2A CN201911279155A CN112979584A CN 112979584 A CN112979584 A CN 112979584A CN 201911279155 A CN201911279155 A CN 201911279155A CN 112979584 A CN112979584 A CN 112979584A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
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Abstract
本发明是关于一种Mannich碱的制备方法。以1,2‑二羟基‑9,10‑蒽醌、哌嗪、甲醛为原料,通氮气隔绝氧气,浓盐酸为催化剂,80℃回流得到粗产品,经过抽滤可得到深紫色目标产物Mannich碱。该目标化合物具有较好的生物活性,对乳腺癌细胞MCF‑7的IC50为30μM。
Description
技术领域
本发明属于化学合成技术领域,涉及一种Mannich碱的制备方法。
背景技术
1-羟基-9,10-蒽醌(茜素)具有良好的抑菌性,以其为原料,对其改性,制备成Mannich碱,该类物质具有良好的生物活性,对乳腺癌细胞MCF-7的IC50为30μM。
发明内容
本发明的目的提供一种新的抗癌物质Mannich碱的制备方法,操作简便、成本低、收率高。
为实现本发明目的,以1,2-二羟基-9,10-蒽醌、4-甲基哌嗪、甲醛为原料,通氮气隔绝氧气,浓盐酸为催化剂,80℃回流得到粗产品,经过抽滤可得到深紫色目标产物Mannich碱。其特征在于合成路线如下:
化合物A 化合物B 化合物C
化合物D
本发明所采用的技术方案表述如下:
(1)甲醛与二级胺混合,乙醇作溶剂,浓HCl催化,回流一段时间。
(2)原料茜素用溶剂溶解后,通入氮气置换出氧气。
(3)将步骤1中的物质慢慢滴入步骤2的混合物,加热回流10h。
(4)将反应得到的粗产品进行抽滤,用溶剂反复洗涤,可得到纯度98%以上的Mannich碱。
本发明具有以下优点:
1、首次合成新Mannich碱1,2-二羟基-3-(4-甲基哌嗪亚甲基)-9,10-蒽醌;
2、产品纯度高,操作简单,后处理简单,成本低,产率高。
具体实施方式
通过下述实例将有助于理解本发明,但以下实例仅用于更具体的说明本发明的优选实施方式,不用于对本发明技术方案的限定。上述本发明的技术方案均为可实现本发明目的的技术方案。即以下实例所采用的温度和试剂,均可用上文所述的相应温度和试剂进行替代。
实施例1
1、化合物D的制备
配备带有磁力搅拌的油浴锅,用乙醇作溶剂将甲醛30mmol与4-甲基哌嗪15mmol混合,滴入2d浓HCl催化,磁力搅拌,80度回流2h。另将茜素(5mmol)置于三颈烧瓶中,通氮气半小时,80度回流10h。
2、化合物D的纯化
反应冷却后,瓶壁上有新的固体产生,抽滤后,用乙醇洗涤,烘干,得深紫色粉末。烘干后即得化合物D,收率78%。元素分析实测值(计算值)/%:C68.18(63.17),H5.71(5.72),O18.17(18.16)N7.94(7.95)F4.75(4.77);1H-NMR( 300MHz, DMSO) δH: 7.6-8.3(m,5H),2.1-3.9(s,13H)。
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2019
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Application publication date: 20210618 |