SU1299502A3 - Способ получени @ -алкилоксимов или их солей - Google Patents

Способ получени @ -алкилоксимов или их солей Download PDF

Info

Publication number: SU1299502A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mol; oxime; phenyl; phenylmethylene; general formula
Prior art date: 1983-02-08

Application number

SU843703074A

Other languages

English (en)

Russian (ru)

Inventor

Будаи Золтан

Мезеи Тибор

Лай Аранка

Петец Луиза

Грашшер Каталин

Сирт Енике

Original Assignee

Эдьт Дьедьсерведьесети Дьяр (Инопредприятие)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-02-08

Filing date

1984-02-08

Publication date

1987-03-23

1984-02-08 Application filed by Эдьт Дьедьсерведьесети Дьяр (Инопредприятие) filed Critical Эдьт Дьедьсерведьесети Дьяр (Инопредприятие)

1987-03-23 Application granted granted Critical

1987-03-23 Publication of SU1299502A3 publication Critical patent/SU1299502A3/ru

Links

150000003839 salts Chemical class 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 31
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
150000002923 oximes Chemical class 0.000 claims abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
150000001340 alkali metals Chemical class 0.000 claims abstract 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
101150068479 chrb gene Proteins 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 28
-1 oxime ethers Chemical class 0.000 abstract description 28
238000002360 preparation method Methods 0.000 abstract description 19
239000002904 solvent Substances 0.000 abstract description 5
229910052757 nitrogen Inorganic materials 0.000 abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
239000002253 acid Substances 0.000 abstract 2
239000004215 Carbon black (E152) Substances 0.000 abstract 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
150000004703 alkoxides Chemical class 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
229930195733 hydrocarbon Natural products 0.000 abstract 1
150000002430 hydrocarbons Chemical class 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000007858 starting material Substances 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000008096 xylene Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
ZMLUHYJUTIZTOJ-UHFFFAOYSA-N 2-dimethylamino-2-methyl-1-chloro-ethane Natural products ClCC(C)N(C)C ZMLUHYJUTIZTOJ-UHFFFAOYSA-N 0.000 description 4
RXYQHVMJQFHKDX-UHFFFAOYSA-N 3-chloro-n,n-di(propan-2-yl)propan-1-amine Chemical compound CC(C)N(C(C)C)CCCCl RXYQHVMJQFHKDX-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000004914 cyclooctane Substances 0.000 description 2
NARWYSCMDPLCIQ-UHFFFAOYSA-N ethane;hydrochloride Chemical compound Cl.CC NARWYSCMDPLCIQ-UHFFFAOYSA-N 0.000 description 2
229960003750 ethyl chloride Drugs 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
VTVVPTRDNLXHFT-PKNBQFBNSA-N (2e)-2-[(4-chlorophenyl)methylidene]cyclohexan-1-one Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(=O)CCCC\1 VTVVPTRDNLXHFT-PKNBQFBNSA-N 0.000 description 1
VCDPHYIZVFJQCD-ZRDIBKRKSA-N (2e)-2-benzylidenecyclohexan-1-one Chemical compound O=C1CCCC\C1=C/C1=CC=CC=C1 VCDPHYIZVFJQCD-ZRDIBKRKSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
HCAHMRPMYBVHGU-UHFFFAOYSA-N 1,2-dimethyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1C HCAHMRPMYBVHGU-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylamino-1-chloro-ethane hydrochloride Natural products CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
244000239634 longleaf box Species 0.000 description 1
DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- 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
- C07D295/08—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 singly bound oxygen or sulfur atoms
- C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU843703074A 1983-02-08 1984-02-08 Способ получени @ -алкилоксимов или их солей SU1299502A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU83415A HU189226B (en)	1983-02-08	1983-02-08	Process for producing basic oxime-ethers

Publications (1)

Publication Number	Publication Date
SU1299502A3 true SU1299502A3 (ru)	1987-03-23

Family

ID=10949516

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU843703074A SU1299502A3 (ru)	1983-02-08	1984-02-08	Способ получени @ -алкилоксимов или их солей

Country Status (11)

Country	Link
JP (1)	JPS59172453A (de)
AT (1)	AT385508B (de)
BE (1)	BE898834A (de)
CH (1)	CH659063A5 (de)
DE (1)	DE3404424A1 (de)
ES (1)	ES8506605A1 (de)
FR (1)	FR2540492B1 (de)
GB (1)	GB2135994B (de)
HU (1)	HU189226B (de)
IT (1)	IT1196016B (de)
SU (1)	SU1299502A3 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU197205B (en) *	1984-07-10	1989-03-28	Egyt Gyogyszervegyeszeti Gyar	Process for production of medical compositions against angine
HU202195B (en) *	1987-12-31	1991-02-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing new substituted styrene derivatives and medical compositions comprising such compounds
US5071853A (en) *	1989-03-23	1991-12-10	Bigge Christopher F	Polycyclic amines useful as cerebrovascular agents
US5180736A (en) *	1989-03-23	1993-01-19	Warner-Lambert Company	Polycyclic amines useful as cerebrovascular agents
HU212415B (en) *	1989-08-25	1996-06-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing new cyclic oxym derivatives and pharmaceutical compositions containing them as active components

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1493222A (en) *	1976-01-27	1977-11-30	Egyt Gyogyszervegyeszeti Gyar	Cycloalkanone oxime ethers and process for the preparation thereof
US4083978A (en) *	1976-01-27	1978-04-11	Egyt Gyogyszervegyeszeti Gyar	Oxime ethers
HU178518B (en) *	1978-12-19	1982-05-28	Egyt Gyogyszervegyeszeti Gyar	Process for preparing cyclododekanone oxime ethers

1983
- 1983-02-08 HU HU83415A patent/HU189226B/hu not_active IP Right Cessation
1984
- 1984-02-02 CH CH480/84A patent/CH659063A5/de not_active IP Right Cessation
- 1984-02-03 BE BE1/010951A patent/BE898834A/fr not_active IP Right Cessation
- 1984-02-07 GB GB08403234A patent/GB2135994B/en not_active Expired
- 1984-02-07 AT AT0038784A patent/AT385508B/de not_active IP Right Cessation
- 1984-02-07 IT IT19469/84A patent/IT1196016B/it active
- 1984-02-07 FR FR8401832A patent/FR2540492B1/fr not_active Expired
- 1984-02-08 JP JP59021514A patent/JPS59172453A/ja active Pending
- 1984-02-08 DE DE19843404424 patent/DE3404424A1/de not_active Withdrawn
- 1984-02-08 ES ES529566A patent/ES8506605A1/es not_active Expired
- 1984-02-08 SU SU843703074A patent/SU1299502A3/ru active

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Патент СССР № 633472, кл. С 07 С 131/02, 1978. *

Also Published As

Publication number	Publication date
FR2540492A1 (fr)	1984-08-10
IT8419469A0 (it)	1984-02-07
DE3404424A1 (de)	1984-08-16
ES529566A0 (es)	1985-08-01
JPS59172453A (ja)	1984-09-29
CH659063A5 (de)	1986-12-31
ATA38784A (de)	1987-09-15
IT1196016B (it)	1988-11-10
GB2135994B (en)	1986-08-20
AT385508B (de)	1988-04-11
ES8506605A1 (es)	1985-08-01
FR2540492B1 (fr)	1988-02-19
BE898834A (fr)	1984-08-03
GB2135994A (en)	1984-09-12
HU189226B (en)	1986-06-30
GB8403234D0 (en)	1984-03-14

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