NO131279B - - Google Patents
Download PDFInfo
- Publication number
- NO131279B NO131279B NO3607/71A NO360771A NO131279B NO 131279 B NO131279 B NO 131279B NO 3607/71 A NO3607/71 A NO 3607/71A NO 360771 A NO360771 A NO 360771A NO 131279 B NO131279 B NO 131279B
- Authority
- NO
- Norway
- Prior art keywords
- camphidine
- substituted
- halide
- condensation
- substituents
- Prior art date
Links
- -1 camphor imide Chemical class 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- CHRAJVQLWOMYQI-SCZZXKLOSA-N (1s,5r)-5,8,8-trimethyl-3-azabicyclo[3.2.1]octane Chemical class C1NC[C@H]2CC[C@]1(C)C2(C)C CHRAJVQLWOMYQI-SCZZXKLOSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 241000723346 Cinnamomum camphora Species 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229960000846 camphor Drugs 0.000 claims description 7
- 229930008380 camphor Natural products 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 1
- CHRAJVQLWOMYQI-UHFFFAOYSA-N 5,8,8-trimethyl-3-azabicyclo[3.2.1]octane Chemical class C1NCC2CCC1(C)C2(C)C CHRAJVQLWOMYQI-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 208000010513 Stupor Diseases 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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60S—SERVICING, CLEANING, REPAIRING, SUPPORTING, LIFTING, OR MANOEUVRING OF VEHICLES, NOT OTHERWISE PROVIDED FOR
- B60S3/00—Vehicle cleaning apparatus not integral with vehicles
- B60S3/002—Vehicle drying apparatus
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60S—SERVICING, CLEANING, REPAIRING, SUPPORTING, LIFTING, OR MANOEUVRING OF VEHICLES, NOT OTHERWISE PROVIDED FOR
- B60S3/00—Vehicle cleaning apparatus not integral with vehicles
- B60S3/04—Vehicle cleaning apparatus not integral with vehicles for exteriors of land vehicles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60S—SERVICING, CLEANING, REPAIRING, SUPPORTING, LIFTING, OR MANOEUVRING OF VEHICLES, NOT OTHERWISE PROVIDED FOR
- B60S5/00—Servicing, maintaining, repairing, or refitting of vehicles
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Drying Of Solid Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE13852/70A SE358352B (ko) | 1970-10-13 | 1970-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131279B true NO131279B (ko) | 1975-01-27 |
| NO131279C NO131279C (ko) | 1975-05-07 |
Family
ID=20298096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3607/71A NO131279C (ko) | 1970-10-13 | 1971-10-01 |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT315002B (ko) |
| BE (1) | BE773833A (ko) |
| CH (1) | CH533027A (ko) |
| DE (1) | DE2148135C3 (ko) |
| DK (1) | DK127687B (ko) |
| FR (1) | FR2111250A5 (ko) |
| GB (1) | GB1348328A (ko) |
| NL (1) | NL7113716A (ko) |
| NO (1) | NO131279C (ko) |
| SE (1) | SE358352B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984921A (en) * | 1974-12-06 | 1976-10-12 | William Charles Adams | Unitary drier |
| FR2541213B1 (fr) * | 1983-02-18 | 1988-10-28 | Sorelec | Dispositif de sechage de moteurs de traction, notamment destines a des locomotives electriques diesel, electriques et automotrices |
| CN106585573B (zh) * | 2017-01-04 | 2020-11-24 | 上海蔚来汽车有限公司 | 电动汽车底盘清洁装置及清洁方法 |
-
1970
- 1970-10-13 SE SE13852/70A patent/SE358352B/xx unknown
-
1971
- 1971-09-27 DE DE2148135A patent/DE2148135C3/de not_active Expired
- 1971-09-27 GB GB4495571A patent/GB1348328A/en not_active Expired
- 1971-10-01 NO NO3607/71A patent/NO131279C/no unknown
- 1971-10-06 NL NL7113716A patent/NL7113716A/xx not_active Application Discontinuation
- 1971-10-12 FR FR7136569A patent/FR2111250A5/fr not_active Expired
- 1971-10-12 CH CH1487271A patent/CH533027A/de not_active IP Right Cessation
- 1971-10-12 DK DK494871AA patent/DK127687B/da unknown
- 1971-10-12 AT AT882571A patent/AT315002B/de not_active IP Right Cessation
- 1971-10-12 BE BE773833A patent/BE773833A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2148135B2 (de) | 1973-12-20 |
| DK127687B (da) | 1973-12-17 |
| FR2111250A5 (ko) | 1972-06-02 |
| NL7113716A (ko) | 1972-04-17 |
| CH533027A (de) | 1973-01-31 |
| DE2148135A1 (de) | 1972-04-20 |
| SE358352B (ko) | 1973-07-30 |
| BE773833A (fr) | 1972-01-31 |
| DK127687C (ko) | |
| DE2148135C3 (de) | 1974-07-11 |
| GB1348328A (en) | 1974-03-13 |
| NO131279C (ko) | 1975-05-07 |
| AT315002B (de) | 1974-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4476136A (en) | Aminomethyl-5 oxazolidinic derivatives and therapeutic use thereof | |
| US5464872A (en) | Arylalkyl (thio) amides | |
| BG60333B2 (bg) | Производни на цис-4-фенил-1,2,3,4-тетрахидро-1-нафталамин с антидепресивно действие | |
| IMMEDIATA et al. | β-Naphthyl derivatives of ethanolamine and n-substituted ethanolamines | |
| SK284428B6 (sk) | Spôsob výroby citalopramu | |
| Hengartner et al. | New syntheses of racemic tryptophans | |
| PT946493E (pt) | Processo de preparacao de um derivado naftalenamina | |
| EA005491B1 (ru) | Способ получения циталопрама | |
| NO131279B (ko) | ||
| MOFFETT et al. | SUBSTITUTED PYRROLIDINES AND PYRROLIDYLETHANOLS1 | |
| US3097207A (en) | 1-halophenyl and 1-alkoxyphenyl cyclohexylamines | |
| Benington et al. | Mescaline analogs. I. 2, 4, 6-trialkoxy-β-phenethylamines | |
| US4705807A (en) | Amine derivatives | |
| JPS6011901B2 (ja) | 新規の脂肪族置換された４−フエニル−ピペリジン | |
| US4146645A (en) | Hypertensive phenylalkylamines and salts thereof | |
| US2793212A (en) | Substituted benzamidopiperidinopropanes | |
| Leonard et al. | Centrally Active 2-(Substituted phenyl)-β-alanines1 | |
| NZ526874A (en) | Process for preparing (+/-) trans-4-p-fluorophenyl-3-hydroxymethyl-1-methylpiperidine | |
| US2837568A (en) | Bis(halophenylimino)cyclohexanes | |
| US3166570A (en) | Derivatives of benzo[e] isoindoline and their preparation | |
| US3320283A (en) | Phenylcyclohexylmethylamine compounds | |
| US3093652A (en) | Alkyl 1-(2-aryl-2-oxoalkyl)-4-phenylpiperidine-4-carboxylates and their preparation | |
| NO142103B (no) | Soppdrepende middel for anvendelse i og paa landbruksprodukter | |
| US3555093A (en) | 2,alpha-dimenthyl-beta-ethyl-beta-(p-fluorophenyl)-ethylamines and the salts thereof | |
| NO743822L (ko) |