CS210993B1 - Preparation method of 1,2,3,4,5,6-hexahydro-1-benzazotin - Google Patents
Preparation method of 1,2,3,4,5,6-hexahydro-1-benzazotin Download PDFInfo
- Publication number
- CS210993B1 CS210993B1 CS928579A CS928579A CS210993B1 CS 210993 B1 CS210993 B1 CS 210993B1 CS 928579 A CS928579 A CS 928579A CS 928579 A CS928579 A CS 928579A CS 210993 B1 CS210993 B1 CS 210993B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hexahydro
- preparation
- toluene
- benzazotin
- aluminum hydride
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 claims description 4
- -1 sodium aluminum hydride Chemical compound 0.000 claims description 4
- VTIJFGNTDHLPLT-UHFFFAOYSA-N 1,2,3,4,5,6-hexahydro-1-benzazocine Chemical compound C1CCCCNC2=CC=CC=C21 VTIJFGNTDHLPLT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Postupom podlá vynálezu sa předmětná -tetrahydro-1-benzazocín-2/1H/-onu vzorca zlúčenina vzorca I získává redukciou 3,4,5,6IIAccording to the process of the invention, the subject -tetrahydro-1-benzazocin-2 (1H) -one of formula (I) is obtained by reduction of 3,4,5,6II
H z?H z?
N—<N— <
/11/ komplexnými a1 umíniumhydr ídmi. Redukci a sa prevádza di-/alkoxy/nátr iumaluminiumhydridmi obecného vzorca III(11) with complex aluminium hydrides. The reduction a is carried out with di- (alkoxy) sodium aluminum hydrides of the formula III
NaAlH2[0/CH2/n0R 2] kde n x 1 až 5 a R je popřípadě rozvětvený alkyl C^-C^, v aromatickom rozpúštadle za varu.NaAlH 2 [O / CH 2 / n OR 2 ] wherein n x 1 to 5 and R is an optionally branched C 1 -C 4 alkyl, in the aromatic solvent at boiling.
Výhodou postupu podlá vynálezu je omnoho vyššia bezpečnost práce, kratsia reakčná doba /6 hod/a vyššie výtažky /80 až 90 %/ oproti dosial používanej metóde. Ďalšou výhodou je používanie tuzemského přípravku di-/raetoxyetoxy/-nátriumalumíniumhydridu proti dovázanému 1 itiumalumíniurahydridu.Advantages of the process according to the invention are much higher work safety, shorter reaction time (6 hours) and higher yields (80 to 90%) compared to the method used up to now. Another advantage is the use of a domestic preparation of di- (methoxyethoxyethoxy) sodium aluminum hydride over imported lithium aluminum hydride.
V dalsom je predmet vynálezu objasněný na příklade bez toho, aby sa na tento výlučné obmedzoval:In the following, the subject matter of the invention is illustrated by way of example without limiting this:
K zmesi 2,75 1 70% roztoku di-/metoxyetocy/nátriuraalumíniumhydridu v toluéne a 2,75 1 bezv. toluénu sa za miešania prikvapká roztok 0,875 kg 3,4,5,6-1 e t r ahyd ro - 1-benzaz-oc ínu-2/lH/-onu v 10 1 bezv. toluénu tak, aby roztok rovnoměrně vřel.To a mixture of 2.75 L of a 70% solution of di- / methoxyetocyte / sodium aluminum hydride in toluene and 2.75 L of aq. of toluene is added dropwise with stirring a solution of 0.875 kg of 3,4,5,6-1-tetrahydro-1-benzazoline-2 (1H) -one in 10 l of anhydrous toluene. toluene so that the solution boils evenly.
Po přidaní sa zmes refluxuje ešte 6 hodin. Po schladeni sa pomaly za miešania přidá 5 1 30% roztoku hydroxidu sodného. Toluénová vrstva sa oddělí a vodná extrahuje 3 1 toluénu. Spojené toluénové vrstvy sa premyjú vodou a vysušia bezv. síranom sodným. Po oddestilovaní toluénu sa zvyšok destiluje vákuovo. Získá sa 0,7 kg /88 %/ 1,2,3,4,5,6-hexahydro-1-benzazocínu t. v. 112 °C/1,33 kPa.After the addition, the mixture was refluxed for a further 6 hours. After cooling, 5 L of a 30% sodium hydroxide solution was added slowly with stirring. The toluene layer was separated and the aqueous extracted with 3 L of toluene. The combined toluene layers were washed with water and dried over anhydrous. sodium sulfate. After toluene was distilled off, the residue was distilled in vacuo. 0.7 kg (88%) of 1,2,3,4,5,6-hexahydro-1-benzazocine is obtained, m.p.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS928579A CS210993B1 (en) | 1979-12-22 | 1979-12-22 | Preparation method of 1,2,3,4,5,6-hexahydro-1-benzazotin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS928579A CS210993B1 (en) | 1979-12-22 | 1979-12-22 | Preparation method of 1,2,3,4,5,6-hexahydro-1-benzazotin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS210993B1 true CS210993B1 (en) | 1982-01-29 |
Family
ID=5443715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS928579A CS210993B1 (en) | 1979-12-22 | 1979-12-22 | Preparation method of 1,2,3,4,5,6-hexahydro-1-benzazotin |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS210993B1 (en) |
-
1979
- 1979-12-22 CS CS928579A patent/CS210993B1/en unknown
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