GB971752A - Phenyl-alkylamines,their manufacture and use - Google Patents
Phenyl-alkylamines,their manufacture and useInfo
- Publication number
- GB971752A GB971752A GB9080/61A GB908061A GB971752A GB 971752 A GB971752 A GB 971752A GB 9080/61 A GB9080/61 A GB 9080/61A GB 908061 A GB908061 A GB 908061A GB 971752 A GB971752 A GB 971752A
- Authority
- GB
- United Kingdom
- Prior art keywords
- appropriate
- benzyl
- reacting
- reducing
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 hydroxy, methoxy, ethoxy Chemical group 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- OKVJCVWFVRATSG-UHFFFAOYSA-N 3-hydroxybenzyl alcohol Chemical compound OCC1=CC=CC(O)=C1 OKVJCVWFVRATSG-UHFFFAOYSA-N 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 abstract 3
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- 150000007522 mineralic acids Chemical group 0.000 abstract 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- PDYCXUZHSKLETQ-UHFFFAOYSA-N (3-ethoxyphenyl)methanol Chemical compound CCOC1=CC=CC(CO)=C1 PDYCXUZHSKLETQ-UHFFFAOYSA-N 0.000 abstract 1
- AFKLSWIRJUJWKY-UHFFFAOYSA-N (3-phenylmethoxyphenyl)methanol Chemical compound OCC1=CC=CC(OCC=2C=CC=CC=2)=C1 AFKLSWIRJUJWKY-UHFFFAOYSA-N 0.000 abstract 1
- ITJWNXBZSFIJTP-UHFFFAOYSA-N 1-(bromomethyl)-3-phenylmethoxybenzene Chemical compound BrCC1=CC=CC(OCC=2C=CC=CC=2)=C1 ITJWNXBZSFIJTP-UHFFFAOYSA-N 0.000 abstract 1
- MBJQDUQVRZNFHX-UHFFFAOYSA-N 2-(3-ethoxyphenyl)acetonitrile Chemical compound CCOC1=CC=CC(CC#N)=C1 MBJQDUQVRZNFHX-UHFFFAOYSA-N 0.000 abstract 1
- CKZFVIPFANUBDW-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)acetonitrile Chemical compound N#CCC1=CC=CC(OCC=2C=CC=CC=2)=C1 CKZFVIPFANUBDW-UHFFFAOYSA-N 0.000 abstract 1
- XKLPCZIDHJNXHH-UHFFFAOYSA-N 2-(4-aminophenyl)-2-ethylbutanenitrile Chemical compound CCC(CC)(C#N)C1=CC=C(N)C=C1 XKLPCZIDHJNXHH-UHFFFAOYSA-N 0.000 abstract 1
- VWLFBXQEYXERSZ-UHFFFAOYSA-N 2-ethyl-2-(4-hydroxyphenyl)butanenitrile Chemical compound CCC(CC)(C#N)C1=CC=C(O)C=C1 VWLFBXQEYXERSZ-UHFFFAOYSA-N 0.000 abstract 1
- DGWATNWJVLWQKU-UHFFFAOYSA-N 2-ethyl-2-(4-nitrophenyl)butanenitrile Chemical compound CCC(CC)(C#N)C1=CC=C([N+]([O-])=O)C=C1 DGWATNWJVLWQKU-UHFFFAOYSA-N 0.000 abstract 1
- NIWOFSGCBJZYJQ-UHFFFAOYSA-N 2-ethyl-2-phenylbutanenitrile Chemical compound CCC(CC)(C#N)C1=CC=CC=C1 NIWOFSGCBJZYJQ-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises phenylalkylamines of the formula <FORM:0971752/C1/1> and physiologically tolerable acid addition salts thereof, wherein OR1 is a hydroxy, methoxy, ethoxy or benzyloxy group, R2 is an alkyl group of 1-4 carbon atoms and R3 and R4 are alkyl groups of 1-4 carbon atoms or, together with the adjacent central carbon atom, represent a saturated acyclic ring system of 5 or 6 carbon atoms. The compounds are prepared by (a) reducing a corresponding primary b -phenylalkylamine in the presence of a ketone of the formula R3-CO-R5 wherein R5 may be an alkyl or an alkenyl group of 1-4 carbon atoms; (b) reacting the appropriate primary b -phenylalkylamine with an ester R3(R4)-CH-X, wherein X is an inorganic or organic acid radical, if desired in the presence of an acid-binding agent; (c) heating the appropriate primary b -phenyl-alkylamine with an alcohol of the formula R3(R4)-CHOH in the presence of Raney nickel; (d) reacting an appropriate b -phenylalkanol with an amine R3(R4)CHNH2; (e) reacting an appropriate b -phenylalkyl halide with an amine R3(R4)-CH-NHR6 wherein R6 is hydrogen or a benzyl group which is subsequently split off by hydrogenation; (f) reducing an appropriate a -phenylaldehyde in the presence of an amine R3(R4)CH-NH2 or (g) reducing the appropriate a -phenylalkanoyl-N-alkylamide with LiAlH4. If the group OR1 in the products is a methoxy, ethoxy or benzyloxy group, it may be treated by known methods for the cleavage of such ethers to give the corresponding hydroxy compound or conversely a hydroxyl group may be etherified to give the methoxy or ethoxy compounds. Primary 2-phenyl-2-alkyl-butylamines used as starting materials are prepared by reducing the corresponding (hydroxy-methoxy-, ethoxy- or benzyloxy-) phenyl-a -ethyl-a -alkyl-acetonitriles, obtainable by heating the corresponding benzyl cyanide with the appropriate alkyl halides in the presence of sodamide. Starting materials bearing a p-hydroxy-substituent may be made via the unsubstituted benzyl cyanide, e.g. 2-(41-hydroxy-phenyl)-2-ethyl-butylamine is made by treating benzyl cyanide with ethyl bromide in the presence of sodamide, nitrating the resulting phenyldiethyl-acetonitrile to 4-nitrophenyl-diethyl-acetonitrile, reducing to 4-aminophenyl-diethyl-acetonitrile, diazotizing and boiling to 4-hydroxyphenyl-diethyl-acetonitrile and hydrogenating. Phenylalkyl halides of the formula R1O-C6H4C(R2)(C2H5) -CH2-Hal are made by reducing phenyl-dialkyl-acetic acids to the carbinols with LiAlH4 and halogenating e.g. with HBr. 3-Ethoxy-benzyl-cyanide is made by etherifying 3-hydroxybenzyl alcohol with diethyl sulphate, reacting the resulting 3-ethoxybenzyl alcohol with HBr to give the bromide and treating with potassium cyanide. 3-Benzyloxy-benzyl-cyanide is made by reacting 3-hydroxybenzyl alcohol with benzyl bromide, reacting the resulting 3-benzyloxybenzyl alcohol with HBr to give 3-benzyloxybenzyl bromide and treating with potassium cyanide. Pharmaceutical preparations having analgesic activity comprise the above compounds of the invention in admixture or conjunction with a pharmaceutical carrier. The preparations preferably take the form of tablets or dragees for oral administration. The active compounds may be used in the form of their addition salts with organic and inorganic acids such as hydrohalic, phosphoric, sulphamic, mono- and di-carboxylic acids and citric, aceturic, aspartic, p-aminobenzoic, salicylic and ethylenediamine-tetracetic acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1960F0030735 DE1242240C2 (en) | 1960-03-11 | 1960-03-11 | Process for the preparation of phenylalkylamines and their acid addition salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB971752A true GB971752A (en) | 1964-10-07 |
Family
ID=7093891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9080/61A Expired GB971752A (en) | 1960-03-11 | 1961-03-13 | Phenyl-alkylamines,their manufacture and use |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3188349A (en) |
| DE (1) | DE1242240C2 (en) |
| GB (1) | GB971752A (en) |
| NL (1) | NL262294A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3422141A (en) * | 1962-01-17 | 1969-01-14 | Haessle Ab | 3,4-dihydroxyphenylalkanamides |
| US3422140A (en) * | 1962-01-17 | 1969-01-14 | Haessle Ab | 2,3-dihydroxyphenylalkanamides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2251245A (en) * | 1938-10-01 | 1941-07-29 | Gen Aniline & Film Corp | Production of hydroxy alkyl amines |
| DE904536C (en) * | 1942-11-29 | 1954-02-18 | Troponwerke Dinklage & Co | Process for the preparation of 1- (oxyphenyl) -2-aminobutanes with an analgesic effect |
| NL64412C (en) * | 1943-08-18 | |||
| US2793977A (en) * | 1951-08-31 | 1957-05-28 | Caspe Saul | Compositions and method for reducing blood sugar concentration |
| US2742397A (en) * | 1953-06-09 | 1956-04-17 | Commercial Solvents Corp | Analgetic compositions of n-(1-methyl propyl) cyclohexylamine |
| US2884455A (en) * | 1956-10-29 | 1959-04-28 | Dow Chemical Co | Propynyl phenylethylamines and their halogen acid salts |
-
0
- NL NL262294D patent/NL262294A/xx unknown
-
1960
- 1960-03-11 DE DE1960F0030735 patent/DE1242240C2/en not_active Expired
-
1961
- 1961-03-08 US US94131A patent/US3188349A/en not_active Expired - Lifetime
- 1961-03-13 GB GB9080/61A patent/GB971752A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1242240B (en) | 1967-06-15 |
| NL262294A (en) | |
| US3188349A (en) | 1965-06-08 |
| DE1242240C2 (en) | 1967-12-07 |
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