GB1003687A - Substituted amines, and processes for their production - Google Patents
Substituted amines, and processes for their productionInfo
- Publication number
- GB1003687A GB1003687A GB24397/63A GB2439763A GB1003687A GB 1003687 A GB1003687 A GB 1003687A GB 24397/63 A GB24397/63 A GB 24397/63A GB 2439763 A GB2439763 A GB 2439763A GB 1003687 A GB1003687 A GB 1003687A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tert
- butyl
- hydroxy
- methyl
- formula
- 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
- 150000001412 amines Chemical class 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 abstract 5
- -1 cinnamic acid nitrile Chemical class 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 125000003277 amino group Chemical group 0.000 abstract 3
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract 2
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 abstract 2
- DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 abstract 2
- 230000021736 acetylation Effects 0.000 abstract 2
- 238000006640 acetylation reaction Methods 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229930016911 cinnamic acid Natural products 0.000 abstract 2
- 235000013985 cinnamic acid Nutrition 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- CAVGWEXCHOHYMM-UHFFFAOYSA-N 1-(3-tert-butyl-4-hydroxy-5-methylphenyl)propan-2-one Chemical compound CC(=O)CC1=CC(C)=C(O)C(C(C)(C)C)=C1 CAVGWEXCHOHYMM-UHFFFAOYSA-N 0.000 abstract 1
- ZMUXHNTXRWEFHE-UHFFFAOYSA-N 1-(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)propan-2-one Chemical compound C(C)(C)(C)C1=C(C(=C(C(=C1)C)CC(C)=O)C)O ZMUXHNTXRWEFHE-UHFFFAOYSA-N 0.000 abstract 1
- ZSUXVFYQNRPSSJ-UHFFFAOYSA-N 2,4-dimethyl-3-[2-(pentylamino)ethyl]phenol Chemical compound C(CCCC)NCCC1=C(C(=CC=C1C)O)C ZSUXVFYQNRPSSJ-UHFFFAOYSA-N 0.000 abstract 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 abstract 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 1
- APIQWHVRWQYLFW-UHFFFAOYSA-N 2-tert-butyl-6-ethylphenol Chemical compound CCC1=CC=CC(C(C)(C)C)=C1O APIQWHVRWQYLFW-UHFFFAOYSA-N 0.000 abstract 1
- HVQTXWREBLUDAI-UHFFFAOYSA-N 3-(2-aminoethyl)-6-tert-butyl-2,4-dimethylphenol Chemical compound C(C)(C)(C)C1=C(C(=C(CCN)C(=C1)C)C)O HVQTXWREBLUDAI-UHFFFAOYSA-N 0.000 abstract 1
- IOFKLPGWURTFMD-UHFFFAOYSA-N 3-tert-butyl-4-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C(C)(C)C)=C1O IOFKLPGWURTFMD-UHFFFAOYSA-N 0.000 abstract 1
- VNONTDVAMQDIJU-UHFFFAOYSA-N 3-tert-butyl-5-ethyl-4-hydroxybenzaldehyde Chemical compound CCC1=CC(C=O)=CC(C(C)(C)C)=C1O VNONTDVAMQDIJU-UHFFFAOYSA-N 0.000 abstract 1
- MAAADQMBQYSOOG-UHFFFAOYSA-N 4-bromo-2-ethylphenol Chemical compound CCC1=CC(Br)=CC=C1O MAAADQMBQYSOOG-UHFFFAOYSA-N 0.000 abstract 1
- XSHVUFSKCNABCE-UHFFFAOYSA-N 4-bromo-2-tert-butyl-6-ethylphenol Chemical compound CCC1=CC(Br)=CC(C(C)(C)C)=C1O XSHVUFSKCNABCE-UHFFFAOYSA-N 0.000 abstract 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 abstract 1
- WODZSHMAILHEGD-UHFFFAOYSA-N 6-tert-butyl-3-(chloromethyl)-2,4-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CCl WODZSHMAILHEGD-UHFFFAOYSA-N 0.000 abstract 1
- GJFZHQACSAOGRD-UHFFFAOYSA-N C(CCC)NCCC1=C(C(=CC=C1C)O)C Chemical compound C(CCC)NCCC1=C(C(=CC=C1C)O)C GJFZHQACSAOGRD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- LEQFNWLPFQYVBT-UHFFFAOYSA-N N-(4-butyl-3-hydroxy-2,6-dimethylphenyl)acetamide Chemical compound C(C)(=O)NC1=C(C(=C(C=C1C)CCCC)O)C LEQFNWLPFQYVBT-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000578 anorexic effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229940117803 phenethylamine Drugs 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229960003424 phenylacetic acid Drugs 0.000 abstract 1
- 239000003279 phenylacetic acid Substances 0.000 abstract 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM0053252 | 1962-06-19 | ||
| DEM0053338 | 1962-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1003687A true GB1003687A (en) | 1965-09-08 |
Family
ID=25987259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24397/63A Expired GB1003687A (en) | 1962-06-19 | 1963-06-19 | Substituted amines, and processes for their production |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3202711A (https=) |
| BE (1) | BE633799A (https=) |
| FR (1) | FR3239M (https=) |
| GB (1) | GB1003687A (https=) |
| NL (1) | NL293886A (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1493960C3 (de) * | 1963-04-25 | 1974-07-18 | Merck Patent Gmbh, 6100 Darmstadt | 2-(3'-tert-Butyl-4'-hydroxy-5'methyl-phenyl)-2-hydroxy-äthylamin, dessen physiologisch verträgliche Säureadditionssalze und Verfahren zu deren Herstellung |
| US3314995A (en) * | 1963-12-09 | 1967-04-18 | Mobay Chemical Corp | Alkylene oxide adducts of bis(2, 4-diamino-5-methyl phenyl)methane |
| HU174125B (hu) * | 1977-03-11 | 1979-11-28 | Egyt Gyogyszervegyeszeti Gyar | Sposob poluchenija novykh n-alkil-proizvodnykh 1-fenil-2-amino-1,3-propandiola |
| US4324717A (en) * | 1980-06-23 | 1982-04-13 | The B. F. Goodrich Company | Norbornene polymers stabilized with hindered aromatic alcohols |
| US4657929A (en) * | 1983-10-25 | 1987-04-14 | Fisons Plc | Compounds |
| JPH0676285B2 (ja) * | 1985-11-01 | 1994-09-28 | 三井東圧化学株式会社 | ベンジルアミン誘導体、その製造法およびその用途 |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) * | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6211244B1 (en) | 1994-10-21 | 2001-04-03 | Nps Pharmaceuticals, Inc. | Calcium receptor-active compounds |
| EP0907631B1 (en) | 1996-05-01 | 2003-06-18 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2480754A (en) * | 1946-10-17 | 1949-08-30 | Gulf Research Development Co | Chromium-containing phenolic amine reaction product |
| US2879294A (en) * | 1956-01-25 | 1959-03-24 | Mead Johnson & Co | 1, 1-diaryl-2-aminoalkanols |
| US2971887A (en) * | 1956-05-30 | 1961-02-14 | Horner Frank W Ltd | Inhibition of isoniazid acetylation |
| US2892753A (en) * | 1957-02-26 | 1959-06-30 | Boehringer Sohn Ingelheim | Central nervous system stimulant |
| US3116330A (en) * | 1959-10-19 | 1963-12-31 | Hoechst Ag | Nu-aminophenylethyl-2, 2-diphenyl-alkylamines |
-
1963
- 1963-06-11 NL NL293886A patent/NL293886A/nl unknown
- 1963-06-19 BE BE633799A patent/BE633799A/fr unknown
- 1963-06-19 US US288874A patent/US3202711A/en not_active Expired - Lifetime
- 1963-06-19 FR FR938610A patent/FR3239M/fr active Active
- 1963-06-19 GB GB24397/63A patent/GB1003687A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE633799A (fr) | 1963-12-19 |
| US3202711A (en) | 1965-08-24 |
| NL293886A (https=) | 1965-04-12 |
| FR3239M (fr) | 1965-04-12 |
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