SU239963A1 - METHOD FOR OBTAINING CYCLIC ENAMINES OF LACTAMS - Google Patents
METHOD FOR OBTAINING CYCLIC ENAMINES OF LACTAMSInfo
- Publication number
- SU239963A1 SU239963A1 SU1218523A SU1218523A SU239963A1 SU 239963 A1 SU239963 A1 SU 239963A1 SU 1218523 A SU1218523 A SU 1218523A SU 1218523 A SU1218523 A SU 1218523A SU 239963 A1 SU239963 A1 SU 239963A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- lactams
- enamines
- obtaining cyclic
- piperidine
- cyclic enamines
- Prior art date
Links
- 150000002081 enamines Chemical class 0.000 title description 6
- 150000003951 lactams Chemical class 0.000 title description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- -1 cyclic enamines Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEIWYFRREFUNRC-UHFFFAOYSA-N hydron;piperidine;chloride Chemical compound [Cl-].C1CC[NH2+]CC1 VEIWYFRREFUNRC-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- YBOFMSCOQHPFRN-UHFFFAOYSA-N 3,3-dichloroazepan-2-one Chemical compound ClC1(Cl)CCCCNC1=O YBOFMSCOQHPFRN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Description
Енамины представл ют собой специфический класс органических соединений и благодар своей высокой реакционной способности могут найти применение в области органического синтеза.Enamines are a specific class of organic compounds and, due to their high reactivity, can be used in the field of organic synthesis.
Предложен способ получени циклических енаминов лактамов общей формулы:A method is proposed for the preparation of cyclic enamines of lactams of the general formula:
x NMe;CH.x NMe; CH.
заключающийс в том, что а,а-дихлорпроизводные лактамов конденсируют с циклическими вторичными аминами, например пиперидином , и целевой продукт выдел ют известными способами. Выход 99D/0.that is, the a, a-dichloro derivatives of lactams are condensed with cyclic secondary amines, for example piperidine, and the desired product is isolated by known methods. Output 99D / 0.
Пример 1. 3-(N-Пипepидил)-2-oкco-2H1 ,5,6,7-тетрагидроазепин (га 2; x CH).Example 1. 3- (N-Piperidyl) -2-oco-2H1, 5,6,7-tetrahydroazepine (ha 2; x CH).
Смесь 24,6 г а,а-дихлоркапролактама и 50 г пиперидина нагревают 2 час при 110°С. В процессе реакции образуетс раствор , из которого выпадает обильный осадок, представл ющий собой смесь енамина (1) и хлоргидрата пиперидина. По охлаждении к реакциоиной массе прибавл ют хлороформ и воду и размешивают до полного растворени осадка. Органический слой промывают водойA mixture of 24.6 g a, a-dichlorocaprolactam and 50 g of piperidine is heated for 2 hours at 110 ° C. During the reaction, a solution is formed, from which a copious precipitate forms, which is a mixture of enamine (1) and piperidine hydrochloride. After cooling, chloroform and water are added to the reaction mass and stirred until the precipitate is completely dissolved. The organic layer is washed with water.
до отмывки хлоргидрата пиперидина и сушат сульфатом натри . Хлороформный раствор упаривают в вакууме досуха. Остаток растирают с эфиром, фильтруют и сушат. Выход целевого продукта (/г 2; х СН.2) 26 г (99,27о от теории), т. пл. 153-155°С. Дл анализа вещество кр11сталлизуют из этилаиетата (1 : 15), т. ил. 156-158°Сuntil piperidine hydrochloride is washed and dried with sodium sulfate. The chloroform solution is evaporated to dryness in vacuo. The residue is triturated with ether, filtered and dried. The yield of the target product (/ g 2; x CH.2) 26 g (99.27 from the theory), so pl. 153-155 ° C. For analysis, the substance is crystallized from ethyl acetate (1:15), i.e. 156-158 ° С
Вычислено, о/о: С 68,04; Н 9,27; N 14,43. CnnisNoO.Calculated, o / o: C 68.04; H 9.27; N 14.43. CnnisNoO.
Найдено, о/„: С 68,03; Н 9.37; N 14,59. Пример 2. 3- 1-Пцперидил-2-оксо-1,2,5,61етрагидропиридин (« 1; А СН2).Found, o / „: C 68.03; H 9.37; N 14.59. Example 2. 3-1-Pcperidyl-2-oxo-1,2,5,61 tetrahydropyridine (“1; A CH2).
Смесь 6,73 г а,а-дцхлорпиперидона-2 и 14 мл пиперидина нагревают 6 час при 110°С. По охлаждении осадок отфильтровывают , обильно прО}|1ывают четыреххлористым углеродом (остаток на фильтре - хлоргидрат пиперидина). Маточный раствор упаривают в вакууме досуха, остаток раствор ют в эфире, фильтруют, маточный раствор уиаривают до небольшого объема, выдел ют 4 г целевого продукта ( л СПо), т. пл. 116-118°С (из эфира).A mixture of 6.73 g a, a-dtshlorpiperidona-2 and 14 ml of piperidine is heated for 6 hours at 110 ° C. After cooling, the precipitate is filtered off, copiously passing over} | 1 with carbon tetrachloride (the residue on the filter is piperidine hydrochloride). The mother liquor is evaporated in vacuo to dryness, the residue is dissolved in ether, filtered, the mother liquor is diluted to a small volume, 4 g of the expected product (l SPo) are isolated, m.p. 116-118 ° C (from ether).
Вычислено, о/о: С 66,66; Н 8.88; N 15,55. ClonioNoO.Calculated, o / o: C 66.66; H 8.88; N 15.55. ClonioNoO.
Пайдено, о/,; С 66,56; П 8,60; N 15,80. Аналогично из дихлоркапролактама и Nметилпиперазина синтезируют енамин (« 2; .), т. пл. 144-145°С (из бензина). 3 Вычислено, о/о; с 63,15; Н 9,09; N 20,09. СиНиЛзО. Найдено, о/о: С 62,92; Н 8,88; N 19,54. Предмет изобретени Способ .получени циклических енаминов лактамов общей формулы:Ю 5 4 /-., , . f l:2 х N- ,х-НМе;СНг отличающийс тем, что а,а-дихлорпроизводные лактамов конденсируют с циклическими вторичными аминами, например пиперидином. и целевой продукт выдел ют известными способами .Paideno, o / ,; C, 66.56; P 8.60; N 15.80. Similarly, enamine is synthesized from dichlorocaprolactam and Nmethyl piperazine (“2;.), T. Pl. 144-145 ° C (from gasoline). 3 Calculated, o / o; c 63.15; H 9.09; N 20.09. SiNiLZO. Found, o / o: C 62.92; H 8.88; N 19.54. The subject of the invention. A method for the preparation of cyclic enamines of lactams of the general formula: S 5 4 / -.,. f l: 2 x N-, x-HMe; CHg characterized in that a, a-dichloro derivatives of lactams condense with cyclic secondary amines, for example, piperidine. and the desired product is isolated by known methods.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU239963A1 true SU239963A1 (en) |
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