SU1299502A3 - Method for producing o-alkyloximes or salts thereof - Google Patents

Abstract

An improved process for the preparation of basic oxime ethers of the general Formula I <IMAGE> /wherein R is a phenyl group optionally substituted by one to three halogen atom/s/ and/or lower alkoxy group/s/; R<1> and R<2> each are hydrogen or together from a valence bond; A is lower alkylene; R<3> and R<4> each stand for hydrogen or lower alkyl or together with the adjacent nitrogen atom they are attached to form a 5-8 membered heterocyclic ring which may optionally contain a further oxygen or nitrogen atom and/or may be optionally substituted by lower alkyl, phenyl or phenyl-lower alkyl, and n is 3, 4, 5, 6 or 7/ and acid addition salts thereof comprises reacting an oxime of the general Formula II <IMAGE> with a compound of the general Formula III <IMAGE> (where Hal is a halogen atom) or an acid addition salt thereof in the presence of an alkali metal lower alkoxide and an aromatic organic hydrocarbon solvent.

Description

one

This invention relates to an improved process for the preparation of 0 -alkyl oximes represented by the general formula

 H (C T -0-A-T .... Rii

e-ng

(I)

AND

where R is phenyl unsubstituted or substituted by 1-3 halogen atoms; R and Rj - hydrogen together form a valence bond} A - lower alkylene

In a flask equipped with a stirrer, 23.57 g (0.1 mol) of 2- (E) - 2 - (m-chlorophenylmethylene) (- cyclohexan-1-one) E-oxime, 150 ml of xylene and 18.9 g (0.35 mol) of sodium methylate and distilled from the reaction mixture with stirring at atmospheric pressure; 30 ml of a mixture of xylene and methanol. Then the temperature of the reaction mixture is reduced to a temperature below the boiling point and 34.2 g (0.11 mol) of M-benzyl-S - (2- t5-chloroethyl) -piperazine dihydrochloride is added to it. The reaction was continued to warm for several more hours.

R, and K - lower alkksht or together

with a nitrogen atom with which 50 ml of solvent is distilled from it,

they are bonded, form pipera-, and then cooled to, vysisinil, which can be quenched in 200 ml of ice water, separated by a lower alkyl, the phenyl-xylene phase, washed with water

until neutral and evaporated under reduced pressure. 38.25 g of the title compound are obtained. Exit 87.3%. The resulting 2- - (E) -butendioate (1/2) has T, nn.197 199.5 C. Mol. weight, 670.2).

Calculated,% J C 60,94; H 6.02 {Cf 5.29; N 6.27. 30 C jH gCtNaO

scrap or phenyl (lower) alkyl, and p 3-6 or their salts.

The purpose of the invention is to increase the yield of the target product.

Example 1: Preparation of 2- (E) - - (2,4-dichlorophenylmethyl) (- 1 -) (E) - (4-benzyl-piper azinylpropoxyimino) -cyclohexane.

150 g of anhydrous toluene, 5.4 g (0.1 mol) of sodium methylate and 27.02 g (0.1 mol) of 2- (E) (2,4-dichlorophenylmethylene) (- cyclohexane -1-; (-one) E1-oxime, about 30 mp of a mixture of methanol and toluene are overtaken from the reaction mixture, then 27.7 g (0.11 mol) S-benzyl are added to it at the boiling point of the mixture - - (3-chloropropyl) -piperazine and 50 ml of toluene. After this, the reaction mixture is left to stand for 1-2 hours and poured into 150 ml of ice water. The toluene solution is washed to neutrality and evaporated at a lower temperature. pressure ultaeum is obtained; 41.94 g of the title compound. Yield: 86.2%, 2- (E) -Butandioate (1/2) plate: 197–200, .Mol. weight. 718.65.

Calculated,%: C 58.3t H 5.75, Ct 9.86, N 5.84.

C, 5H4, C, N, 0 ,.

Found,%: C 58.4, H 5.69 $ C1 9.79; N 5.87.

UV 273 nm (e 15409).

Example 2. Getting 2-C (E) - - (m-chlorophenylmethylene) (1) (E)

Found,%: C 61.04, H 6.13 $ Ct 5.25, - N 6.31.

y S s Awoist .274 nm (8 15246), Example 3. Preparation of (- -phenylmethylene -) (E) - (4-phenylpiperazinyl-propoxyimino)) -cyclohexane. The process is carried out in the same manner as described in Example 1, with .Q the difference that 20.1 g (0.1 mol) (phenylmethylene-cycl-hexan-1-one) of E-oxime are used as the starting compounds. and 25.0 g (0.105 mol) of L-phenyl for - (3-chloroprope saw) -piperazine. As a result, 35.19 g of the title compound are obtained. The yield is 87.2%. Hydrochloride has it. PC. 190-194 ° C. Mol weight. 440.04. : Calculated,%: C, 70.97; H 7.79;

50

55

cr 8.06; N 9.55.

C, 6H, 4C1N, 0

Found,%: C 71.06; H 7.83 / C 8.11; N 9.61.

Example 4. Preparation of 2-f (E) - - (o-chlorophenylmethylene) (- 1 -) (E) - (4 - -benzylpiperazinylpropoxyimine) - -diclohexane.

The process is carried out in the same manner as described in Example 2, c.

995022

-ben zilpiper azinylate oxyimino) -cyclohexane.

In a flask equipped with a stirrer, 23.57 g (0.1 mol) of 2- (E) - 2 - (m-chlorophenylmethylene) (- cyclohexan-1-one) E-oxime, 150 ml of xylene and 18.9 g (0.35 mol) of sodium methylate and distilled from the reaction mixture with stirring at atmospheric pressure; 30 ml of a mixture of xylene and methanol. Then the temperature of the reaction mixture is reduced to a temperature below the boiling point and 34.2 g (0.11 mol) of M-benzyl-S - (2- t5-chloroethyl) -piperazine dihydrochloride is added to it. The reaction was continued to warm for several more hours.

Found,%: C 61.04, H 6.13 $ Ct 5.25, - N 6.31.

y S s Awoist .274 nm (8 15246), Example 3. Preparation of (- -phenylmethylene -) (E) - (4-phenylpiperazinyl-propoxyimino)) -cyclohexane. The process is carried out in the same manner as described in Example 1, with the difference that 20.1 g (0.1 mol) (phenylmethylene-cyclH-hexan-1-one) E-oxime and 25 , 0 g (0.105 mol) L-phenyl to - (3-chloropropyl) -piperazine. As a result, 35.19 g of the title compound are obtained. The yield is 87.2%. Hydrochloride has it. PC. 190-194 ° C. Mol weight. 440.04. : Calculated,%: C, 70.97; H 7.79;

50

55

cr 8.06; N 9.55.

C, 6H, 4C1N, 0

Found,%: C 71.06; H 7.83 / C 8.11; N 9.61.

Example 4. Preparation of 2-f (E) - - (o-chlorophenylmethylene) (- 1 -) (E) - (4 - -benzylpiperazinylpropoxyimine) - -diclohexane.

The process is carried out in the same manner as described in Example 2, c.

3

the difference that 23.57 g (0.1 mol) of 2- (E) - (s-chlorophenylmethylene) (- cyclohexan-1-one) E-oxime and 35.72 g (0 , 11 mol) M-benzyl-m - (3-chloropropyl) -piperazine dihydrochloride and. 37.71 g of the desired compound are obtained. The yield is 83.4%. 2 - (E) -Butendioate (1/2) of the obtained compound had an mp. 197-201 S. Mol. weight 68.2.

Calculated,%: C 61.44, H 6.15, Ct 5.19; N 6.14.

C35H4., CtN, 04

Found,%: C 61, 6.22,

Cf 5.16; N 6.23 UV:

269 named (11573). p 5. Getting 2- (E) max

Prime

-phenylmethylene) (- 1 -) (E) - (4 -benzylpipperazinylethoxyimino) -cyclopentane. 20

The process is carried out in the same manner as described in Example 1, with the difference that 21.53 g are used as starting compounds.

The process is carried out in the same manner as described in Example 1, with the difference that 23.6 g (0.1 mol) 2- (E) - (p-chloro-phenylmethylene) ( -cyclohexan-1-one) E1-oxime and 19.54 g (0.11 mol) of 1-diisopropyl-amino-3-chloropropane. 37.14 g of the desired compound are obtained, yield 98.5%. 2- (E) -Butendioate (1/1) has m. Pl. 87-89 ,. Mol weight, 493.06.

Calculated,%; Ct 7.19; N 5.68.

C.gH.CtN. 63.34; H 7.56;

Found,%: C 63.22; H 7.49, Ct 7.18; N 5.72.

UV: max 280 nm (5 17456), Example 8, Preparation of 2- (Z) -phenylmethylene) (-1-) (2-diisoprosch (0.1 mol) (phenylmethylene cyclo-25 amino-ethoxyimipo) -cyclopentane, pentan-1-one) E-oxime and 26.16 g. The process is carried out in the same way

(0.11 mol) N-benzyl-N - (2-chloroethyl) - as described in example 2, with that of piperazine. The result is

the difference is that 21.53 g are used as starting compounds

38.8 g of the title compound. Output

the difference is that 21.53 g are used as starting compounds

93.2%. The dihydrochloride of the indicated co-ZO (0.1 mol) (phenylmethylene-cyclopene / an-1-one) E-oxime and 22.02 g (0.11 mol) of 1-diisopro PIlamino-2-chloro-ethane-hydrochloride, B This gives 31.3 g of the title compound. Yield 91.4%. The 2- (E) -Buentiato (1/1) has a melting point of 117-120 ° C. Mol weight, 458.6,

Dineni has so pl. 206-209 S. Mol. weight. 489.62.

Calculated,%: C, 66.23; H 7.43, Ct 14.56; N 8.58.

With „ПзбС№ 0

Found,%: C 66.12; H 7.15; C 14.62-, N 8.61.

UV: L1a | ks 262 nm (e 17012).

Example 6. Preparation of 2- (E) - -phenylmethylene) (- 1 - / (E) -) 3 -diisopropylaminopropoxyimino) -cyclohexane

The process is carried out in the same manner as described in Example 1, with the difference that 20.13 g (0.1 mol) (-phenylmetsh1en-cyclohexan-1-one-) E-oxime are used as starting compounds. and 19.53 g (0.11 mol) of 1-diisopropylamino-3-chloropropane. 33.05 g of the desired compound are obtained. The yield of 96.5% .2- (E) -Butendioate (1/1) has an mp. 130-13 ° C Mol weight. 458.61.

Calculated,%: C 68.09; H 8.35; N 6.10.

Czb jgN Oj Found, 6.03,

UV: LMrks

C, 67.95; H 8.42;

 275 nm.

0

five

0

Example 7. Obtaining 2-f (E) - (p-chloro-phenylmethylene) (- 1 -) (E) - (3 - diisopropylamino-propoxyimino) - cyclohexane.

The process is carried out in the same manner as described in Example 1, with the difference that 23.6 g (0.1 mol) 2- (E) - (p-chloro-phenylmethylene) ( -cyclohexan-1-one) E1-oxime and 19.54 g (0.11 mol) of 1-diisopropyl-amino-3-chloropropane. 37.14 g of the desired compound are obtained, yield 98.5%. 2- (E) -Butendioate (1/1) has m. Pl. 87-89 ,. Mol weight, 493.06.

Calculated,%; Ct 7.19; N 5.68.

C.gH.CtN. 63.34; H 7.56;

Found,%: C 63.22; H 7.49, Ct 7.18; N 5.72.

as described in example 2, with that

the difference is that 21.53 g are used as starting compounds

(0.1 mol) (phenylmethylene cyclo

(0.1 mol) (phenylmethylene cyclo

pen / an-1-one) E-oxime and 22.02 g (0.11 mol) of 1-diisopro PIlamino-2-chloro-ethane hydrochloride, In Tata, 31.3 g of the title compound are obtained. Yield 91.4%. The 2- (E) -Buentiato (1/1) has a melting point of 117-120 ° C. Mol weight, 458.6,

%: C 68.09, AND 8.35;

N

Calculated,), 11.

.O

C, 67.92; H, 8.42;

Found, N 6.07.

UV: Ama.s 258 nm (11182). Example 9. Obtaining 2- (E) - - (p-chloro-phenylmethylene) (- 1 -) (E) - (2 - -dimethylamino-ethoxyimino) -cyclohexane.

The process is carried out in the same manner as described in Example 1, with the difference that 23.57 g (0.1 mol) 2- (E) - (p-chloro-phenylmethylene) (-cyclohexane -1-on) E1-oxime and 12.24 g (0.105 mol) 1 - dimethyl-n--2-chloroethane. 28.60 g of the desired compound are obtained. Yield 93.2%. 2- (E) -Butendioate (1/1) has m. Pl. 168.5-171 ° C. Mol weight. 422.92.

Calculated,%: C 59.64, H 6.44, - Ct 8.38; N 6.62. C, j, H,

-Found,%: C 59.425 H 6.38} C 8.27 N 6.67.

UV5 "ako 275 nm (19292). Example 10. Preparation of 2-benzyl-1- (E) - (2-dimethylamino-ethoxy-amino) 3-cyclopentane.

The process is carried out in the same manner as O as described in Example 2, with the difference that 21.63 g (0.1 mol) of 2-benzine 1-cyclopentane-1 ethane hydrochloride are used as starting compounds, and instead of xylene, toluene is used as a solvent. The result is 27.51 g of the desired compound. Exit 87.5%. 5 2- (E) -Butendioate (1/1) has so pl. 86-88 ° C. Mol weight.430,53.

Calculated,%: C 66.95j H 7.96, N 6.51.

.OS

Found,%: C 67,12; And 8.04; N6.58.

UV T motsso 264 them (16395).

Example 13. Preparation of 2- (E) - -phenylmethylene) (-) (E) - (2 -diisopropyl-on- (E) -oxime and 16.84 g (0.11 mol) f5 of amino-ethoxyimino) -cyclohexane .

2-dimethylamino-1-chloro-ethane-hydrochloride. The result is 26.96 g of the desired compound. Yield 93.5%. 2- (E) -Bootendis (1/1) has so pl. 121 ° C. Mol weight 404.51.

Calculated,%: C 65.32 H 7.97, N 6.93.

C ,, H ,,.

Found,% C 65.47, H-7.82, N 6.95.

Example 11. Preparation of 2- (E) - -phenylmethylene) (- 1 -) (E) - (4-methyl-piperazinyl-propoxyimino) -cyclopentane.

The process is carried out in the same manner as described in Example 1, with the difference that 21.5 g (0.1 mol) of 2- (E) -phenylmethylene-cyclopentane-1 are used as compounds. The process is carried out in the same way as described in example 1, with the difference that 20.13 g are used as starting compounds

20 (0.1 mol) 2- (E) -phenylmethyl-cyclohexan-1-one (E) 1-oxime and 18.00 g (0.11 mol) of 1-diisopropylamino-2- -chlorozane. The result is 31.71 g of the desired compound. Output

25 96.3%. 2- (E) -Butendioate has so pl. 103-105 ° C. Mol weight. 444.58.

Calculated,%. C 67.54, H 8.16, N 6.30.

Ci5 36NiOs 30 Found: C, 67.23; H 8.32;

. N 6.28.

ccc 275 nm (17304). Example 14. Obtaining 2- (E) - -phenylmethylene - I- (E) - (3 -dimethyl-he (E) -oxime and 18,55 g (0,105 mol) 35 propoxyimino) -cyclooctane.

N-MeTmi-N - (3-chloro-Shch) -piperazi-Process is carried out in the same manner as described in Example 1, with the difference that 22.93 g 40 (0.1 mol ) 2- (E) -phenylmethylene-cyclo-octan-1-one- (E) oxime and 15.11 g (0.11 mol) of 1-dimethylamino-3-chloropropane; benzene . 45 28.40 g of the desired compound are obtained. Yield 94.5%. 2- - (E) -Butendioate (1/1) has so pl. 136-139 s. Mol weight. 416.52.

C, 66.32; H 7.75;

on, and instead of toluene, the reaction is carried out in benzene. 34.67 g of the target compound are obtained. Yield 93.8%. 2- (E) -Butendioate (1/2) has m. Pl. 204-208 ° C. Mol weight 601.71.

Calculated,%: C 61.88, - H 6.98} N 7.20s

,

Found,%: C 61.62, H 6.87; N 7.17.

  272 nm (1370).

Example 12. Preparation of 2- (E) - (-phenylmethylene) (- 1.-) (E) - (2 dimesh1- 50 N6,73. Amino ethoxyimino) -cyclopentane.

The process is carried out in the same manner as described in Example 2, with the difference that 21.53 g (0.1 mol) of 2- (E) -phenylmethylene-cyclopentane-1-on- (E) -oxime and 18.7 g (0.105 mol) of 1-diethylamino 2-chloroClean,%

Found,%: C 65.89; H 7.64; N 6.79.

UV: L "" KS 276 nm (6 14395). 55 Example 15. Preparation of 2- (E) (phenylmethylene) -1- (E) - (2-dime-. Thiamino-2-methyl ethoxyimino) -cyclo-texane.

95026

ethane hydrochloride, and instead of xylene, toluene is used as a solvent. The result is 27.51 g of the desired compound. Exit 87.5%. 5 2- (E) -Butendioate (1/1) has so pl. 86-88 ° C. Mol weight.430,53.

Calculated,%: C 66.95j H 7.96, N 6.51.

.OS

Found,%: C 67,12; And 8.04; N6.58.

UV T motsso 264 them (16395).

Example 13. Preparation of 2- (E) - -phenylmethylene) (-) (E) - (2 -diisopropylamino-ethoxyimino) -cyclohexane.

The process is carried out in the same manner as described in Example 1, with the difference that 20.13 g are used as starting compounds.

20 (0.1 mol) 2- (E) -phenyl-methyl-cycle of hexan-1-on (E) 1-oxime and 18.00 g (0.11 mol) of 1-diisopropylamino-2- -chlorozane. The result is 31.71 g of the desired compound. Output

25 96.3%. 2- (E) -Butendioate has so pl. 103-105 ° C. Mol weight. 444.58.

Calculated,%. C 67.54, H 8.16, N 6.30.

Ci5 36NiOs 30 Found: C, 67.23; H 8.32;

. N 6.28.

ccc 275 nm (17304). Example 14. Obtaining 2- (E-phenylmethylene - I- (E) - (3 -dimethyl 35 propoxyimino) -cyclooctane.

73

Calculated,%

50 N6.73.

Found,%: C 65.89; H 7.64; N 6.79.

UV: L "" KS 276 nm (6 14395). 55 Example 15. Preparation of 2- (E) (phenylmethylene) -1- (E) - (2-dime-. Thiamino-2-methyl ethoxyimino) -cyclo-texane.

71

The process is carried out in the same manner as described in Example 1, with the difference that 20.13 g (0.1 mol) 2 (E) -phenylmethylene-cyclohexan-1-one (E) are used as starting compounds. oxime and 16.6 g (0.105 mol) of 2-dimethylamino-2-methyl -1-chloroethane. 26.9 g of the title compound are obtained. Yield 93.9%. 2- (E) -Butendioate (1/1). It has

square 113-117 S. Mol. weight. 402.48. Calculated,%: C 65.64} H 7.51

N 6.96.

,

NMdone,%: C 65.42, H 7.39; N 6.87.

UV: A / "C1x 273 nm (e 13475).

Example 16. Preparation of 2- - (E) Fensch-1 (-1-) (E) - (2-Dimethylamino-2-methyl-ethoxyimino) -cyclopentane.

The process is carried out in the same manner as described in Example J, with the difference that 21.53 g (0.1 mol) of 2- (E) -phenylmethylene-cyclopentane-1-on- (E) -oxime and 16.6 g (0.105 mol) of 2-dimethylamino-2-methyl--1-chloroethane. 28.61 g of the desired compound are obtained. The yield is 95.2%. 2- (E) -Butendioate (1/1) has m. Pl. 120-123 C.

Calculated,%: C 66.32} H 7.75j

N 6.73.

40

Found,%: C 66.18} H, 7.62; N 6.65.

  262 nm (b 17595).

Example 17. Preparation of 2- - (E) -phenylmetsh1en (-1-) (E) - (2 -di- isopropylamino-ethoxyimino) -cyclo-octane.

The process is carried out in the same manner as described in Example 1, with 45 the difference that 22.93 g (0.1 mol) of 2- (E) -phenylmethylene-cyclo-6ctan-1-one are used as starting compounds. - (E) -oxime and 22.02 g (0.11 mol) of 1-diisopropylamino-2-chloro-ethane. The result is

33.22 g of the title compound. Output q-j 07

7 J, /.

The resulting compound hydrochloride

The process is carried out in the same manner as described in 2, the difference being that 24.97 g of ego (30.1 mol) 2- (E) - (m-chloro-phenipmetylene) and 35 are used as starting compounds. ,

- (3-chloropropyl) -piperazine dihydrochloride. The result is 39.02 g of the desired compound. The yield is 86.5%. 2- (E) -Butendioate (1/2) have T.Sh1. 196-198 ° C. Weight 684.20.

Calculated: C 61.44} H 6.18} Cf 5.18} N 6.14.

C, 5H, CfN, 0,

Found,%: C 61.34} H, 6.32; Ct 5.17; N 6.25.

(, 1cc 274 nm (13700).

Example 20 (comparative) 50 2- (E) - (p-Chlorophenylmethane) (- 1 -) (E - (3-diisopropyl-amino-propoxy-imo) -cyclohexane.

To 50 cm of absolute toluene-containing suspension of 2.4 g (0.1 mol) -g

I mol /.- '/ -pc-chloro-fensh1me n) (-cyclopentan-1-one (E) -oxime i, 72 g (0.11 mol) N-benzyl-n has t. Sh1. 158-161 C. Mol. Weight. -393, sodium carbonate is added dropwise at

Calculated,%: C, 70.29; H 9.47 Ct 9.02 j N 7.13. .

0

five

0

0

five

Found,%: C 69.78; H 9.32; C 9.11; N 7.32.

 Ф: 276 nm (14170).

Example 18. Preparation of 2- (E) - (p-chloro-phenylmethylene) -1- (E) - (h -methyl-piperazinyl-propoxyimino) -cyclohexane.

The process is carried out in the same manner as described in Example 1, with the difference that 23.57 g (0.1 mol) of 2- (E) - (p-chloro-phenylmethylene) - cyclohexan-1-one (E) -oxime and 18.55 g (0.105 mol) N-methyl-K - (3-chloro-propiopyperazine, and xylene is used as a reaction medium instead of toluene, 34 are obtained, 49 g of the title compound. The yield is 87.6%. The 2- (E) -Butendioate (1/1) has a melting point of 196-199 ° C.

Calculated,%: C 57.28; H 6.29} Ct 5.83; N 6.91.

,

Found,%: C 57.32; H 6.37; 5 Ct 5.78; N 6.82.

UV: 1 max 278 nm (16507).

Example 19. Obtaining 2-G (E) - - (m-chlorophenylmethylene) (- 1 -) (E) -4 - -benzyl-piperazinyl-propoxyimino) - 0-cyclopentane.

The process is carried out in the same manner as described in 2, with the difference that 24.97 g g (30.1 mol) 2- (E) - (m-chloro-phenipmethylene) and 35,

- (3-chloropropyl) -piperazine dihydrochloride. The result is 39.02 g of the desired compound. The yield is 86.5%. 2- (E) -Butendioate (1/2) has T.Sh1. 196-198 ° C. Weight 684.20.

Calculated: C 61.44} H 6.18} Cf 5.18} N 6.14.

C, 5H, CfN, 0,

Found,%: C 61.34} H, 6.32; Ct 5.17; N 6.25.

(, 1cc 274 nm (13700).

Example 20 (comparative). 0 2- (E) - (p-Chlorophenylmethyl) (- 1 -) (E) - - (3 -diisopropyl-amino-propoxy-imino) -cyclohexane.

To 50 cm of absolute toluene-containing suspension of 2.4 g (0.1 mol) -gidI mol /.- / –cm-chlor-fensh1me- n) (-cyclopentan-1-one (E) -oxime i, 72 g (0.11 mol) L-benzyl-n 85 C with constant stirring. solution 23.6 g (0.1 mol) 1- (E) - (n- -chlorophenylmethylene) -cyclohexane-1-

30 ° С

-one (E) -oxime in 200 cm of absolute toluene. The mixture is kept for 2 hours at 130 ° C and then a solution of 19.54 g (0.11 mol) of 1-diisopropyl-amino-3-chloro-propane in 20 cm of absolute toluene is added with further stirring. After a further 6 h of heating, the toluene-containing reaction mixture, cooled below, is washed with 100 cm of water and the aqueous solution of 15 g (0.1 mol) is extracted with tartaric acid. The cooled to 0-5 C aqueous solution is made alkaline and then with concentrated ammonium hydroxide solution until the pH is set to 10. The base is extracted with dichloroethane. The solvent is removed in vacuo, and the residue is purified by fractional vacuum distillation. T. Kip. 182-186 ° C (53.3 Pa). Product weight 17.5 g. 2- (E) - Bundy Dioxide (1/1).

17.5 g of base are dissolved in 18 cm of acetone. 75 cm of a hot alcohol-containing solution of 7.33 g of fumaric acid is added to this solution. After cooling, the crystals are dried and dried. Yield 12.09 g (48.7%), t. Sh1. 88-90 ° C, mol. weight 493.06.

Calculated,%: C 63.34; H 7.56 Cr 7.19; N 5.68.

Found,%: C 63.48; H 7.50;

Cf 7.22i N 5.66.

UV L "ax 280 nm (17456).

According to the proposed method (example 7), the yield is 98.5%, and by a known method only 48.7%.

Thus, the proposed method allows to double the yield of the target product.

Editor N. Margolin

Compiled by L.Ioffe

Tehred L. Serdyukova Proofreader AO Bruchar

905/63

Circulation 372 Subscription VNIIPI USSR State Committee

for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5

Production and printing company, Uzhgorod, st. Project, 4

JO f5 20

Formula and

ten

3 o

bratis

,

JO f5 20

25 - 30

The method of obtaining O-alkyloximes of the general formula

.

(SShp C N-0-A-1 C4 |,

R-C-RI H

R

where R R and

A - R. and

P

unsubstituted or substituted by 1–3 halogen atoms, phenyl, R — hydrogen together form a valence bond of lower alkylene; R is lower alkyl or together with the nitrogen atom form piperizinyl, which may be substituted by lower alkyl, phenyl, phenyl (lower) alkyl} 3-6

or their salts by reacting the oxime of the general formula

(

In N

where R, R ,, Rg and p are specified

value i

with haloalkylamine general formula

Na1-A-1 С

at

where R and R have the indicated values in an aromatic hydrocarbon medium, characterized in that, in order to increase the yield of the target product, the process is carried out in the presence of a lower alkali metal salt.

Claims (1)

Claim The method of obtaining O-alkiloximes of General formula In ₃ (SVDp c = N-0-AN <, R-C-Hi n where R is unsubstituted or substituted 1-3 halogen atoms of phenyl; R ₍ and R ₂ - hydrogen together form a valence bond; A is lower alkylene; and R ₄ is lower alkyl or together with the nitrogen atom form piperazinyl, which may be substituted with lower alkyl, phenyl, phenyl (lower) alkyl; η = 3-6 or their salts by the interaction of an oxime of the general formula (cHrb C = N-0H GV _g B-CR, H where R, R ,, R ₂ and n have the indicated meanings with hapoidalkylamine of the general formula / Vc Hcd-AX Bl ;. where R ₃ and R ₄ have the indicated meanings "in an aromatic hydrocarbon medium, characterized in that, in order to increase the yield of the target product, the process is carried out in the presence of lower alkali metal apogoholate.