• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    METHOD FOR OBTAINING AMINO-SUBSTITUTED PHYLENETACONITRILES OF THE FORMULA, 4RS - CH2-CH2-CHg-N-CHg-CHA. where n, K, k3 is hydrogen-, trifluoromethyl or -alkoxy; R, R is C —C-alkyl; , ,, R and ,, -C-alkoxy group, by reacting a cyanogenic mathic compound with alkarylamine in an organic solvent medium at a temperature of from 20 ° C to where R, R2, R-3, R4 have the aforementioned crys, as the alkarylamine compound of the general formula f shn-CH5 where R, R, R have the indicated values, and the process is carried out in the presence of formic acid at molar QQ ratios cyanaline: alkarylamine: /,. formic acid 1: 0.9-1.5: 0.5 / -1.5. :. . QQ
    公开号:SU1083905A3
    申请号:SU813329945
    申请日:1981-09-09
    公开日:1984-03-30
    发明作者:Кастнер Герхард；Зигель Хардо；Гейсс Карл-Хейнц
    申请人:Басф Аг (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a method for the preparation of aminr-substituted phenylacetyl nitriles, which are used in medicine. A method of producing amino-substituted phenylacetonitriles is known, which consists in the fact that substituted pheny acetonitrile condenses with propacoldehyde with co-hydroxy acetal by boiling in toluene in the presence of Na amide, the cyanoacetal is washed with an aqueous solution of oxalic acid in acetone to give a suitable amide with sodium amide, to get the cyanacetate using an aqueous solution of oxalic acid in acetone to give a sodium amide to a suitable cyanate to get a proper rake, to get a proper rake the reduction of aminations with phenylethylamine in ethyl alcohol in the presence of hydrogen and a palladium catalyst at 40-45 C 13, the disadvantage of this method is its many diynosti. The closest to the present invention is a method for producing substituted phenylacetonitriles of the formula C5N C- (CH2) jrW- (CH2W where A, B, C is hydrogen, halogen, lower ;, alkyl, lower alkoxy, R and Rj lower alkyl, n - 2.3 , 4,, 2,3, which consists in the fact that the phenylacetonitrile of the formula where, C -, - K - has the indicated values, is condensed with an amine of the formula (C5H2) "rK - (OH2) r-X R where A, B , C, p, have the indicated meanings; X is a halogen, in the presence of a basic condensing agent (suspension of amide Na) in an organic medium, solvent at room temperature or in boiling. The disadvantage of this method is the experimental difficulties associated with the use of amides, as well as the relatively low yield of the target product. The purpose of the invention is to simplify the process and increase the yield of the target product. amino-substituted phenylacetonitriles of the formula sn-ong-sn-k-si-f DL R / R hydrogen, trifluoromethyl or C —Cf-alkoxy; R, is alkyl; k and R-C -, - C (j-alkoxygroup, by the interaction of cyanaldehyde of the formula C) | -C CH2 CH2CJHO where R, R, R, R .-. have the indicated values, are reacted with alkarylamine of the formula W-CH2-CH, where R, R °, R - have the indicated values in the presence of formic acid at a temperature from 20 ° C to boiling the reaction mass in an organic: solvent medium and a molar ratio of cyanaldehyde: alkarylamine, formic acid 1: 0.9-1, 5: 0.9-1.5. Example. To a solution of 275 g (1 mol) o (-isopropyl-° C - (y-oxpropyl) -veratrilcyanide and 194 g (1 mol) of I-methylhomoverathrlamine (MGVA) in 1.6 l of toluene was added 51 g (g / mol) 90% formic acid and boil., ... ... -,;:;:: After cooling the reaction solution, the aqueous phase is treated with sulfuric acid to a pH of 2-4 and extracted with toluene. Then neutralized with NaOH and extracted with toluene. The toluene phase is washed with water, evaporated under vacuum, and 431 g (95%) of colorless oil are obtained. Name 2-12; Analogously to Example 1, Example 2-12 is carried out according to Table 1.
    T a 6 l and c a 1
    PRI me R 13-17. Analogously to example 1, examples 13-17 are carried out.
    Examples are 18-25. Similarly to example 1, examples 18-25 are carried out,
    at different reaction temperatures, 30 according to table 2.
    Table 2
    However, instead of toluene, a different solvent is used, according to Table. 3, t a b l 1 Hz a 3. 10839 PRI-MER 26. Similarly, ipy 1 is prepared from 305, g (1 mol) - t isopropyl-ot .- (-oxopropyl) g34 trickette. C 1 -benyl nitrile and 194 g (1 mol) of N-methylgomoveratylamine in 51 g {1 Mole) of 90% formic acid 5 get 455 g (94%) of L-isopropyl-c-C (K-metvd1-1-homoveratr1) y-aminopropyl (-5,4,5-trimethoxyphenylcephonitrile. Example 27 Analogously to Example 1, py 1 is obtained from 313 g (1 mol) of yL isopropyl-оС- (y-oxopropyl) -3 - tri05 fluoromethylbenzylnitrile and 194 g (l / I mol) of methylhomoveratrilamine in 46 g (1 mol) of formic acid are obtained 425 g (92%) L-isopropyl-o (N-methyl-N-homoveratri ) -3-aminopropyl -.- triftormetilfenilatsetonitril. The advantage of the proposed method consists in the simplification of the process associated with the use of a metal amide and povshenii the yield (84-100%).
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING.
    Of valuable phenylacetonitriles ι
    CHj - CHg — N — CH2 - '- “27'L" * * 7 ->
    where Κ ^, Κ ^, Η 3 is hydrogen ·, trifluoromethyl or a C ^ -C 6 alkoxy group;
    .. R, R — C ^ -C ^ -alkyl;
    R ° and R 7 are Ό 1 -C ^ alkoxygroup, by the interaction of cyano-containing aro; of a mathematical compound with alkarylamine in an organic solvent at a temperature of from 20 ° С to the boiling point of the reaction mixture, which is due to the fact that, in order to simplify the process and increase the yield of the target product, we use call (cyanaldehyde of the General formula. C-CH 2 - CH 2 CHO f
    R 1 .
    where R 1 , R Z , R · 3 , R 4 'have the indicated meanings, as an alkarylamine compound of the general formula
    Oh, where R ff , R ^, R 7 have the indicated meanings, and the process is carried out in the presence of formic acid at a molar ratio of cyanaldehyde: alkarylamine: formic acid = 1: 0.9-4.5: 0.9 / -1, 5.
    JV>
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE894118C|1943-03-10|1953-10-22|Albert Ag Chem Werke|Process for the preparation of ª ‰, ª ‰ -diphenyl-ethylamines disubstituted on the nitrogen|
    FR2663M|1961-04-01|Knoll Ag|Phenylacetonitriles substituted with basic groups.|
    NL302258A|1962-12-19|
    DE2059923C3|1970-12-05|1979-01-25|Knoll Ag, 6700 Ludwigshafen|1-a-Isopropyl-o - [ v-aminopropyl] -3,4-dimethoxyphenylacetonitrile, process for its preparation and pharmaceuticals containing it|
    JPS5118940B2|1971-12-25|1976-06-14|
    AT331217B|1974-02-05|1976-08-10|Thomae Gmbh Dr K|PROCESS FOR THE PRODUCTION OF NEW AMINOBENZYLAMINES AND THEIR ACID ADDITION SALTS|
    DE2631222C3|1976-07-12|1979-01-04|Knoll Ag, 6700 Ludwigshafen|Process for the preparation of basic substituted phenylacetonitriles|EP0165322B1|1984-06-15|1988-01-20|LUDWIG HEUMANN & CO GMBH|Method for the preparation of phenylacetonitrile substituted by a basic radical|
    US4612329A|1984-10-17|1986-09-16|Hokuriku Pharmaceutical Co., Ltd.|Pharmaceutical alpha-aminoalkyl-alpha-alkylphenylacetonitriles|
    DE3603032A1|1986-01-31|1987-08-06|Basf Ag|BASICLY SUBSTITUTED PHENYL ACETONITRILES, THEIR PRODUCTION AND THE MEDICINAL PRODUCTS CONTAINING THEM|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19803034221|DE3034221A1|1980-09-11|1980-09-11|METHOD FOR PRODUCING BASICLY SUBSTITUTED PHENYL ACETONITRILE|
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