GB700097A - Process of producing 4-(n-phenyl-n-benzyl)-amino-1-alkyl-piperidines and their derivatives substituted in the aromatic radicals - Google Patents
Process of producing 4-(n-phenyl-n-benzyl)-amino-1-alkyl-piperidines and their derivatives substituted in the aromatic radicalsInfo
- Publication number
- GB700097A GB700097A GB18157/50A GB1815750A GB700097A GB 700097 A GB700097 A GB 700097A GB 18157/50 A GB18157/50 A GB 18157/50A GB 1815750 A GB1815750 A GB 1815750A GB 700097 A GB700097 A GB 700097A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- benzyl
- dihydrochloride
- methylpiperidine
- piperidine
- 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
- -1 alkoxy radical Chemical class 0.000 abstract 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 4
- 229940073608 benzyl chloride Drugs 0.000 abstract 4
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 4
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 229960002523 mercuric chloride Drugs 0.000 abstract 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 abstract 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 abstract 1
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 abstract 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 abstract 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 150000001398 aluminium Chemical class 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises 4-(N-phenyl-N-benzyl)-amino-1-alkylpiperidines and their derivatives substituted in either or both of the aromatic nuclei by one halogen, alkyl or alkoxy radical, and a process for preparing the above compounds by boiling 1-alkyl-piperidine-4 with aniline or its halogen, alkyl or alkoxy mono nuclear substituted derivative, reducing the Schiff's bases thus obtained to secondary amines and boiling their N-alkali metal derivatives with benzyl chloride or its halogen, alkyl or alkoxy mono-nuclear substituted derivatives. In the examples: (1) 1-methyl-piperidone-4 is boiled with aniline, the resulting imino compound is boiled with aluminium activated with mercuric chloride to form 4-N-phenylamino-1-methyl-piperidine (the dihydrochloride salt is mentioned) which is reacted with sodamide and benzyl chloride to form 4-(N-phenyl-N-benzyl)-amino-1-methyl piperidine and the dihydrochloride is mentioned; (2) 1-methyl-piperidone-4 is heated with p-anisidine and the resulting imino compound is reduced as in (1) to form 4-(N-41-methoxyphenyl)-amino-1-methyl-piperidine (the dihydrochloride salt is also mentioned) which is converted to 4-(N-41-methoxyphenyl - N - benzyl) - amino - 1 - methyl - piperidine and the dihydrochloride is mentioned; (3) 4 - (41 - methoxybenzyl - anilino) - 1 - methyl piperidine (the dihydrochloride is also mentioned) is prepared by reacting 4-N-phenylamino-1-methyl-piperidine (prepared as in (1)) with sodamide and then p-methoxy-benzyl chloride; (4) 4 - (41 - methoxybenzylanilino) - 1-methyl-piperidine (the dihydrochloride is also mentioned) is prepared as in (3) using 4-methylbenzyl chloride; (5) 4-(41-chlorbenzyl-anilino)-1-methylpiperidine (the dihydrochloride is also mentioned) is prepared as in (3) using 4-chlorbenzyl chloride; (6) 4-(N-41-brombenzylanilino) -1-methylpiperidine (the dihydrochloride is also mentioned) is prepared as in (3) using 4-brombenzyl bromide; (7) 1-methylpiperidine-4 and p-toluidine are boiled and the resulting imino compound is reduced with aluminium chloride activated with mercuric chloride to give 4-(41-methylanilino)-1-methylpiperidine (the dihydrochloride is also referred to) which is then reacted with sodamide and benzyl chloride to give 4 - (N - benzyl - 41 - methylanilino) - 1 - methylpiperidine; (8) 1-methyl-piperidone-4 is condensed with cumidine and the resulting imino compound is reduced as in (7) to give 4 - (41 - isopropylanilino) - 1 - methylpiperidine (the dihydrochloride is also referred to) which is then reacted with sodamide and 4-(41-isopropylanilino)-1-methylpiperidine; (9) 3-chloroaniline and 1-methylpiperidone-4 and the resulting imino compound is reduced with activated aluminium to give 4-(31-chloranilino)-1-methylpiperidine which is then reacted with benzyl chloride to give 4-(N-benzyl-N-31-chlorophenyl)-amino-1-methylpiperidine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE295833X | 1949-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB700097A true GB700097A (en) | 1953-11-25 |
Family
ID=6090179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18157/50A Expired GB700097A (en) | 1949-07-20 | 1950-07-20 | Process of producing 4-(n-phenyl-n-benzyl)-amino-1-alkyl-piperidines and their derivatives substituted in the aromatic radicals |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT170868B (en) |
| CH (1) | CH295833A (en) |
| DK (1) | DK78744C (en) |
| GB (1) | GB700097A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0503411B1 (en) * | 1991-03-14 | 1995-11-29 | BASF Aktiengesellschaft | Substituted N-phenylpiperidines and medicaments thereof |
-
1950
- 1950-07-05 DK DK223150A patent/DK78744C/en active
- 1950-07-07 AT AT170868D patent/AT170868B/en active
- 1950-07-11 CH CH295833D patent/CH295833A/en unknown
- 1950-07-20 GB GB18157/50A patent/GB700097A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK78744C (en) | 1955-01-17 |
| AT170868B (en) | 1952-04-10 |
| CH295833A (en) | 1954-01-15 |
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