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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1960F0030735 DE1242240C2 (de) | 1960-03-11 | 1960-03-11 | Verfahren zur Herstellung von Phenylalkylaminen und deren Saeureadditionssalzen |
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 (enExample) |
| DE (1) | DE1242240C2 (enExample) |
| GB (1) | GB971752A (enExample) |
| NL (1) | NL262294A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3422140A (en) * | 1962-01-17 | 1969-01-14 | Haessle Ab | 2,3-dihydroxyphenylalkanamides |
| US3422141A (en) * | 1962-01-17 | 1969-01-14 | Haessle Ab | 3,4-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 (de) * | 1942-11-29 | 1954-02-18 | Troponwerke Dinklage & Co | Verfahren zur Herstellung von analgetisch wirkenden 1-(Oxyphenyl)-2-amino-butanen |
| NL64412C (enExample) * | 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/de 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 (de) | 1967-06-15 |
| DE1242240C2 (de) | 1967-12-07 |
| US3188349A (en) | 1965-06-08 |
| NL262294A (enExample) |
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