SU495825A3 - Способ получени аминоэфиров - Google Patents

Способ получени аминоэфиров

Info

Publication number: SU495825A3
Authority: SU; USSR - Soviet Union
Prior art keywords: diphenyl; hydrochloride; methoxy; methyl; ethoxy
Prior art date: 1972-09-11

Application number

SU1957929A

Other languages

English (en)

Russian (ru)

Inventor

Хеллингер Родерих

Вендтландт Вольф

Шнайдер Герда

Original Assignee

Хеми Линц Акциенгезельшафт (Фирма)

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.)

1972-09-11

Filing date

1973-09-10

Publication date

1975-12-15

1973-09-10 Application filed by Хеми Линц Акциенгезельшафт (Фирма) filed Critical Хеми Линц Акциенгезельшафт (Фирма)

1975-12-15 Application granted granted Critical

1975-12-15 Publication of SU495825A3 publication Critical patent/SU495825A3/ru

Links

239000002253 acid Substances 0.000 claims description 8
-1 aralkelyl Chemical group 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000000304 alkynyl group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000004305 biphenyl Substances 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
IJDVREQJIQGPHH-UHFFFAOYSA-N 4-cyclopropyl-1-ethoxy-n-methyl-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)C(NC)CCC1CC1 IJDVREQJIQGPHH-UHFFFAOYSA-N 0.000 description 1
MGELZRFDIMUBMC-UHFFFAOYSA-N C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)C(C)CNCC=CC1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)C(C)CNCC=CC1=CC=CC=C1 MGELZRFDIMUBMC-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
PLWUKNBSCFWWBW-UHFFFAOYSA-N Cl.C=1C=CC=CC=1C(CCNCCC=CC)(OCC)C1=CC=CC=C1 Chemical compound Cl.C=1C=CC=CC=1C(CCNCCC=CC)(OCC)C1=CC=CC=C1 PLWUKNBSCFWWBW-UHFFFAOYSA-N 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241000256856 Vespidae Species 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
QFSWEWNANAHUNE-UHFFFAOYSA-N alimadol Chemical compound C=1C=CC=CC=1C(CCNCC=C)(OC)C1=CC=CC=C1 QFSWEWNANAHUNE-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
FDLVCUOMIAFXNG-UHFFFAOYSA-N methyl(propyl)azanium;chloride Chemical compound Cl.CCCNC FDLVCUOMIAFXNG-UHFFFAOYSA-N 0.000 description 1
JTQVKRXONMISDA-UHFFFAOYSA-N n-(3-ethoxy-3,3-diphenylpropyl)but-2-en-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC=CC)(OCC)C1=CC=CC=C1 JTQVKRXONMISDA-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Addiction (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

SU1957929A 1972-09-11 1973-09-10 Способ получени аминоэфиров SU495825A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT776472A AT319916B (de)	1972-09-11	1972-09-11	Verfahren zur Herstellung von neuen basischen Äthern

Publications (1)

Publication Number	Publication Date
SU495825A3 true SU495825A3 (ru)	1975-12-15

Family

ID=3599253

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1957929A SU495825A3 (ru)	1972-09-11	1973-09-10	Способ получени аминоэфиров

Country Status (18)

Country	Link
JP (1)	JPS5320033B2 (2)
AT (1)	AT319916B (2)
BE (1)	BE804692A (2)
CA (1)	CA986138A (2)
CH (2)	CH590206A5 (2)
CS (1)	CS203904B2 (2)
DD (1)	DD108521A1 (2)
ES (1)	ES418687A1 (2)
FI (1)	FI56826C (2)
FR (1)	FR2198740B1 (2)
GB (1)	GB1377350A (2)
HU (1)	HU166685B (2)
LU (1)	LU68308A1 (2)
PL (2)	PL92115B1 (2)
RO (2)	RO63980A (2)
SE (1)	SE413892B (2)
SU (1)	SU495825A3 (2)
ZA (1)	ZA737200B (2)

1972
- 1972-09-11 AT AT776472A patent/AT319916B/de not_active IP Right Cessation
1973
- 1973-08-24 FR FR7330701A patent/FR2198740B1/fr not_active Expired
- 1973-08-27 LU LU68308A patent/LU68308A1/xx unknown
- 1973-08-29 FI FI2684/73A patent/FI56826C/fi active
- 1973-09-04 HU HUCE962A patent/HU166685B/hu unknown
- 1973-09-06 CA CA180,396A patent/CA986138A/en not_active Expired
- 1973-09-06 GB GB4206373A patent/GB1377350A/en not_active Expired
- 1973-09-10 DD DD173374A patent/DD108521A1/xx unknown
- 1973-09-10 PL PL1973183330A patent/PL92115B1/pl unknown
- 1973-09-10 CH CH835576A patent/CH590206A5/xx not_active IP Right Cessation
- 1973-09-10 SU SU1957929A patent/SU495825A3/ru active
- 1973-09-10 ZA ZA737200*A patent/ZA737200B/xx unknown
- 1973-09-10 SE SE7312280A patent/SE413892B/xx unknown
- 1973-09-10 CH CH1294973A patent/CH596144A5/xx not_active IP Right Cessation
- 1973-09-10 BE BE135522A patent/BE804692A/xx unknown
- 1973-09-10 PL PL1973165129A patent/PL86974B1/pl unknown
- 1973-09-11 RO RO7300076047A patent/RO63980A/ro unknown
- 1973-09-11 RO RO7384229A patent/RO68417A/ro unknown
- 1973-09-11 JP JP10176373A patent/JPS5320033B2/ja not_active Expired
- 1973-09-11 ES ES418687A patent/ES418687A1/es not_active Expired
- 1973-09-11 CS CS736291A patent/CS203904B2/cs unknown

Also Published As

Publication number	Publication date
FI56826B (fi)	1979-12-31
CS203904B2 (en)	1981-03-31
CH596144A5 (2)	1978-02-28
FR2198740A1 (2)	1974-04-05
GB1377350A (en)	1974-12-11
PL86974B1 (en)	1976-06-30
RO68417A (ro)	1981-09-24
AT319916B (de)	1975-01-10
SE413892B (sv)	1980-06-30
PL92115B1 (en)	1977-03-31
FI56826C (fi)	1980-04-10
ES418687A1 (es)	1976-02-16
HU166685B (2)	1975-05-28
DD108521A1 (2)	1974-09-20
CA986138A (en)	1976-03-23
JPS5320033B2 (2)	1978-06-24
RO63980A (fr)	1978-08-15
LU68308A1 (2)	1973-11-23
JPS4962452A (2)	1974-06-17
FR2198740B1 (2)	1977-01-14
BE804692A (fr)	1974-03-11
AU6018473A (en)	1975-03-13
ZA737200B (en)	1974-08-28
CH590206A5 (2)	1977-07-29

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