JPS5750965A - Preparation of n-methyl-4-benzazonine derivative - Google Patents
Preparation of n-methyl-4-benzazonine derivativeInfo
- Publication number
- JPS5750965A JPS5750965A JP12628080A JP12628080A JPS5750965A JP S5750965 A JPS5750965 A JP S5750965A JP 12628080 A JP12628080 A JP 12628080A JP 12628080 A JP12628080 A JP 12628080A JP S5750965 A JPS5750965 A JP S5750965A
- Authority
- JP
- Japan
- Prior art keywords
- benzazonine
- formula
- derivative
- compound
- methyl
- 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.)
- Pending
Links
- RAYLESKNYREMMJ-UHFFFAOYSA-N 4-methyl-4-benzazonine Chemical class CN1C=CC=C2C(=CC=C1)C=CC=C2 RAYLESKNYREMMJ-UHFFFAOYSA-N 0.000 title 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 4
- BDNJXCPWLLNGMV-UHFFFAOYSA-N 4h-4-benzazonine Chemical class C1=CNC=CC=C2C=CC=CC2=C1 BDNJXCPWLLNGMV-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 235000019253 formic acid Nutrition 0.000 abstract 2
- 229910052987 metal hydride Inorganic materials 0.000 abstract 2
- 150000004681 metal hydrides Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 230000002829 reductive effect Effects 0.000 abstract 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
- XMWIRHHXZICAHD-UHFFFAOYSA-N 1-methyl-11-azatricyclo[7.4.1.02,7]tetradeca-2(7),3,5-trien-4-ol Chemical compound C1C2CC3=CC=C(O)C=C3C1(C)CCNC2 XMWIRHHXZICAHD-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- -1 lithium aluminum hydride Chemical compound 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
PURPOSE: To prepare the titled compound useful for the medical use, economically, in an industrial scale, in high yield, with simplified process, by the reduction and N-methylation of a 4-benzazonine derivative having no substituent group at the N-position.
CONSTITUTION: A 4-benzazonine derivative of formula I ( R and R' are H or lower alkyl ), e.g. 10-hydroxy-1-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine, is made to react with the compound of formula XCOOY (X is halogen; Y is lower alkyl, alkenyl, or aralkyl) or with formic acid in a solvent, and the product is reduced with a complex metal hydride such as lithium aluminum hydride to obtain the objective compound of formula II. As an alternative method, the compound of formula II can be prepared by the reductive reaction of the 4-benzazonine derivative of formula I with formaldehyde in the presence of formic acid, a complex metal hydride, or hydrogen activated by a catalyst such as Raney-nickel.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12628080A JPS5750965A (en) | 1980-09-11 | 1980-09-11 | Preparation of n-methyl-4-benzazonine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12628080A JPS5750965A (en) | 1980-09-11 | 1980-09-11 | Preparation of n-methyl-4-benzazonine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5750965A true JPS5750965A (en) | 1982-03-25 |
Family
ID=14931298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12628080A Pending JPS5750965A (en) | 1980-09-11 | 1980-09-11 | Preparation of n-methyl-4-benzazonine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5750965A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110563605A (en) * | 2018-06-05 | 2019-12-13 | 上海医药工业研究院 | Intermediate for preparing etazocine hydrobromide and preparation method thereof |
-
1980
- 1980-09-11 JP JP12628080A patent/JPS5750965A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110563605A (en) * | 2018-06-05 | 2019-12-13 | 上海医药工业研究院 | Intermediate for preparing etazocine hydrobromide and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS54122253A (en) | Preparation of cis-alkylcyclohexanol | |
| JPS5750965A (en) | Preparation of n-methyl-4-benzazonine derivative | |
| JPS5223145A (en) | Process for preparing a modified polyolefin composition | |
| CA2131474A1 (en) | Preparation of hydroxyoxaalkylmelamines | |
| JPS57131777A (en) | Preparation of piperazine derivative | |
| JPS56104839A (en) | Preparation of acetic acid and/or methyl acetate | |
| ATE111973T1 (en) | METAL PROTECTIVE COMPOSITIONS, THEIR PRODUCTION PROCESS AND METAL PROTECTION METHOD. | |
| JPS56103197A (en) | Novel d-glucose derivative and antitumor agent containing the same as active constitutent | |
| JPS51113823A (en) | Process for preparation of cis-epoxysuccinic acid salts | |
| JPS57109753A (en) | Preparation of meta-substituted-n-methylaniline derivative | |
| ES8601097A1 (en) | Preparation of agent for treating respiratory trouble | |
| JPS55136281A (en) | Xanthine derivative | |
| JPS5484549A (en) | Priduction of 2-chloro-5-aminotoluene-4-sulfonic acid or its salt | |
| JPS57192354A (en) | Preparation of highly-concentrated transparent liquid ammonium higher secondary alcohol ethoxysulfate | |
| JPS56164148A (en) | Preparation of 7- 3-isopropylamino-2-hydroxypropoxy indene | |
| JPS55133357A (en) | Preparation of 1-cyano-2-hydroxy-3-phthalimidopropane | |
| JPS5754167A (en) | Pyroglutamic acid derivative and its preparation | |
| JPS5699448A (en) | Preparation of lower alkoxyaniline | |
| JPS6233139A (en) | Production of 2-aminobenzyl alcohol | |
| JPS57109789A (en) | 1,2,3,4-tetrahydropyrazino(1,2-a)benzimidazole derivative | |
| JPS55127365A (en) | Preparation of substituted indole | |
| JPS5626821A (en) | Preparation of alpha-aminoacrylic acid derivative | |
| JPS53119822A (en) | Preparation of 2-dimethylaminoethylisothiocyanate | |
| JPS549225A (en) | Preparation of hydrazinoalkanesulfonic acid derivatives | |
| JPS55120541A (en) | Preparation of hydroxyphenylacetatic acid ester |