GB984363A - Organic chemical compounds and methods - Google Patents
Organic chemical compounds and methodsInfo
- Publication number
- GB984363A GB984363A GB2291461A GB2291461A GB984363A GB 984363 A GB984363 A GB 984363A GB 2291461 A GB2291461 A GB 2291461A GB 2291461 A GB2291461 A GB 2291461A GB 984363 A GB984363 A GB 984363A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrochloride
- give
- magnesium
- piperidinomethyl
- chloro
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 8
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 abstract 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 3
- YHPWAILJEPQMRO-UHFFFAOYSA-N 1-[(2-bromophenyl)methyl]piperidine Chemical compound BrC1=CC=CC=C1CN1CCCCC1 YHPWAILJEPQMRO-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 150000003509 tertiary alcohols Chemical class 0.000 abstract 2
- NOYASZMZIBFFNZ-UHFFFAOYSA-N (2-bromophenyl)methanamine Chemical compound NCC1=CC=CC=C1Br NOYASZMZIBFFNZ-UHFFFAOYSA-N 0.000 abstract 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 abstract 1
- LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- MAJHSSWRKQHUEH-UHFFFAOYSA-N N-benzyl-2-(piperidin-1-ylmethyl)benzenecarbothioamide Chemical compound C(C1=CC=CC=C1)NC(C1=C(C=CC=C1)CN1CCCCC1)=S MAJHSSWRKQHUEH-UHFFFAOYSA-N 0.000 abstract 1
- UALLQPOZUXEDOU-UHFFFAOYSA-N N-phenyl-2-(piperidin-1-ylmethyl)benzamide Chemical compound N1(CCCCC1)CC1=C(C(=O)NC2=CC=CC=C2)C=CC=C1 UALLQPOZUXEDOU-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 abstract 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004675 formic acid derivatives Chemical class 0.000 abstract 1
- 238000011534 incubation Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 150000002680 magnesium Chemical class 0.000 abstract 1
- 150000002901 organomagnesium compounds Chemical class 0.000 abstract 1
- JTIBYJGTPOXJMK-UHFFFAOYSA-N phenyl-[2-(piperidin-1-ylmethyl)phenyl]methanol Chemical compound N1(CCCCC1)CC1=C(C(C2=CC=CC=C2)O)C=CC=C1 JTIBYJGTPOXJMK-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- -1 pyrrolidino, piperidino Chemical group 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 150000003556 thioamides Chemical class 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises organomagnesium compounds of formula <FORM:0984363/C2/1> where NR1R2 is a dialkylamino group or a cyclic aliphatic tertiary amino group (such as pyrrolidino, piperidino or 4-alkyl piperazino) and has a total of not more than 8 carbon atoms. They may be prepared by warming magnesium powder or granulated magnesium with a 2-bromobenzylamine of formula <FORM:0984363/C2/2> (where NR1R2 is as above defined) and then adding anhydrous ether. A crystal of iodine may be added during the initial incubation period. Example I describes the preparation of the magnesium complex of N-2-bromobenzylpiperidine. N - 2 - bromobenzylpiperidine is prepared by reacting 2-bromobenzyl bromide with distilled piperidine in anhydrous ether. The magnesium complexes may be reacted with aldehydes to give secondary alcohols, ketones to give tertiary alcohols, with esters to give ketones and thence tertiary alcohols, with isocyanates to give amides and with isothiocyanates to give thioamides. Reaction with formic acid derivatives will give aldehydes. The following compounds are prepared and described: Ex. 2, racemic 4-chloro-21-piperidinomethyl benzhydrol, its hydrochloride and methiodide, 4 - chloro - 21 - dimethylaminomethyl benzhydrol and hydrochloride, 2-methylaminomethyl - 2151 - dimethoxybenzhydrol and hydrochloride, 3,4,5 - trimethoxy - 21 - piperidinomethylbenzhydrol and hydrochloride, 3,4,5 - trimethoxy - 21 - pyrrolidinomethylbenzhydrol and 2 - piperidinomethylbenzhydrol and its hydrochloride hemihydrate: Ex. 3, 4-chloro - 21 - dimethylaminomethyl triphenyl methanol and its hydrochloride hemihydrate, 4,41 - dichloro - 211 - piperidinomethyl triphenyl methanol, its hydrochloride and hydrochloride dihydrate, 4,41 - dimethoxy - 211 - piperidinomethyltriphenylmethanol and hydrochloride hemihydrate, 4,41 - dimethoxy - 211 - pyrrolidinomethyl triphenylmethanol and hydrochloride and 1 - phenyl - 1 - 21 - pyrrolidinomethyl phenylpropanol and hydrochloride hemihydrate: Ex. 4, 2-bromo-21-piperidinomethyl-benzophenone and hydrochloride: Ex. 5, 2-piperidinomethylbenzanilide and Ex. 6, N-benzyl - 2 - piperidinomethylthiobenzamide and its hydrochloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2291461A GB984363A (en) | 1961-06-23 | 1961-06-23 | Organic chemical compounds and methods |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2291461A GB984363A (en) | 1961-06-23 | 1961-06-23 | Organic chemical compounds and methods |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB984363A true GB984363A (en) | 1965-02-24 |
Family
ID=10187104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2291461A Expired GB984363A (en) | 1961-06-23 | 1961-06-23 | Organic chemical compounds and methods |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB984363A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3728460A (en) * | 1968-12-20 | 1973-04-17 | Boehringer Sohn Ingelheim | Anorectic pharmaceutical composition containing certain {60 -(methylamino-methyl)-alpha-(4{40 -halo-phenyl)-benzyl alcohols as active ingredients |
| EP0418013A2 (en) * | 1989-09-11 | 1991-03-20 | Arch Development Corporation | Direct magnesiation of organic materials |
| WO1993022472A1 (en) * | 1992-04-23 | 1993-11-11 | Merck Patent Gmbh | Use of organo-metallic compounds for precipitating metals on substrates |
| EP1046640A2 (en) * | 1999-04-21 | 2000-10-25 | Clariant GmbH | Process for preparing substituted phenyl boronic acids |
-
1961
- 1961-06-23 GB GB2291461A patent/GB984363A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3728460A (en) * | 1968-12-20 | 1973-04-17 | Boehringer Sohn Ingelheim | Anorectic pharmaceutical composition containing certain {60 -(methylamino-methyl)-alpha-(4{40 -halo-phenyl)-benzyl alcohols as active ingredients |
| EP0418013A2 (en) * | 1989-09-11 | 1991-03-20 | Arch Development Corporation | Direct magnesiation of organic materials |
| EP0418013A3 (en) * | 1989-09-11 | 1991-08-28 | Arch Development Corporation | Direct magnesiation of organic materials |
| WO1993022472A1 (en) * | 1992-04-23 | 1993-11-11 | Merck Patent Gmbh | Use of organo-metallic compounds for precipitating metals on substrates |
| EP1046640A2 (en) * | 1999-04-21 | 2000-10-25 | Clariant GmbH | Process for preparing substituted phenyl boronic acids |
| EP1046640A3 (en) * | 1999-04-21 | 2002-07-24 | Clariant GmbH | Process for preparing substituted phenyl boronic acids |
| US6576789B1 (en) | 1999-04-21 | 2003-06-10 | Clariant Gmbh | Process for the preparation of substituted phenylboronic acids |
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