DE2044530A1 - Process for the preparation of basic substituted 2,3 dihydro 1,4 benzoxazm 3 ones - Google Patents

Description

Method jsur Εθτβ division of basic substituted 2 * _t 5

The invention relates to a process for the production of iron 2 _f 3 "Diliydro-l _i 4-benssoxaaiB- * 3-one" of the general formula I as well as their addition salts and external compounds. In formula I, "B ^ eiaaon aliphatic, araliphatic or aromatic heat, the gögendeafalla nooh further subs tu tu th bear tema _t % ^e * ^nö ^ ¹ ^^ *" ° ^ ^β2? A ^ y ^^^ tPP ⁹ * a Halogen-, Hrifluorinetliyl «, nitro, amino, acylaraino-, ilydroxy- or alkoxy radical, A is a straight-chain or linked alkylenvest with 2 to 6 carbon atoms and R ^ a primary, secondary or cyclic araino radical with the `` nitrogen atoms to which !! © th ^ lengrupp © is bound, mean.

2,3-Dihyciro-1,4-DertsoxaEin-3-one eatapreohend the general formula 1 are not yet known.

The aim of the present invention is to synthesize »ouch? Production of basic substituted 2.5 * Bihydro »1,4-ben2Oxaei] aau Find.

BATH ORIGINAL

10983.4 / 1 664

2O44S30

The basic substituted compounds mentioned corresponding to the general formula 1 are obtained by adding 2,3-Bib3rdro »l ₉ 4 -benBoxaein-3-ones of the general formula II, while B ^ and Bg * have the meanings given above with tin © ® reactive © ® Est © r a aminoalcohols eggs general Feme I IH ₉ where I is a reactive group * example Einern halide or "ulfonsUurerest, © $ tspri © Sst and B ^ and a are as defined above, ia Q @ ^ mi & set of alkaline condensation ^ rnittsl uinsetst »

? @ 3fbin <iwiig © n ä®T all ^ emsin ^ n 'Form®! I also receive nan, inder.i aas dl © - S ^ I ^ Difeyteo-lg ^ liemsioxagin-S-ona dei * allneaeinen f®mmt Ϊ1 m®Tst mtfc compounds of the general formula IV ₁ where X dl © has the requirements given above um JY sin Ilaloscnatom seia shall "and then with amines dor general formula V,

Meaning corresponds to, umsotat "

These B @ akti @ B © m wesdüi in 'organieohen Xösun ^ smittel ₉ v / ie s 3 "hiSSis ^ esi alipSiatieohen or aromatic Kohlonwasoer" stoffen "Alk @ 5iol # n _g Eet ^ ra ^ Iet © B®a © der in . wclosriijen ilediea

As a KondeneatlonsoitteX -roresuggest Hkftll «öd @ f frdalkali'verblndunsen, such as Natriumfateiifflihyäroxid, Chewing hydroxide, sodium ethylate VatvivMMBtdy

e9fladt! tt against & 0en basisoli substituted 2,3-dihydro-

a"! High-boiling oils σ? he low-Subftt «i» ee » _t the calibrated in acids and organic

Si · ®2? £ iüd! Iiigge »8essenten bonds show in animal experiments

trad positive inotropic effects.

ei "d Jedceh anti-inflammatory marriages, anti-analgesic effects" which are observed in the harmful forms "w @ in an over-

liagenrertr ^ ldohfeeit feet «·. is created. The questionnaire is explained by the following examples

BATH ORIGINAL

1088347 1854

- 3 Example 1

IA ₉ S & a ^^ Dil ^ dro-li ^ bemoxaBia-J-on, 4 »7 g! Iatritsüeu & iä and 12.8 g ß-Bimeti ^ laiainoäthylohlorid in 2oo ml xylene is heated to the boil for 3 hours» After cooling sucked off, there? The solvent is distilled off and the residue is distilled in a high vacuum. 17.2 g of a pale yellow oil of 4-Cβ-Diisnet} $ l £ u; iinoathyl) -2, ^ are obtained

has a boiling point of 137 ^d C at o _# 25! Dorr.

Duroh '"Tfiaoetaung 32iit Metliyljodid eateteht EIA colorless Metajodid with eineoi Öoliniölspunltt of 264 ⁰ C.

Example 2 ■

16 _S 3 s Ä-I _t »eth _r vl ^ 2 _l 3-dil ^ dro-l _i 4-benBoxaein-3-on become» tsa one. Each amount of 2.6 g of sodium is poured into Zqq al abefolutew alcohol, heated in the bath and slowly 17.6 g of ß-piperidinoyl chloride dripped out. £ th & allows £ h, under reflux boiling "sow ^ t ab / distilled sueret the alcohol and then in the Hoöhvalcutffii Uilcfcstand, In a Siedepwnlct 148-149 ⁰ C and ο" 15 Sorr..destillieren 2o, 3 g of 4- ( ß-Pipöridino-Uth ^ l-aHaethyl ^ i ^ -dihydro-l ^ benBoxassin-S-on as a near, light yellow »l over,;

Example 3 '■■ ■ (

26, above-mentioned Zp-ChlorxJionyl-P-jJ-dihydro-1 ^ beaeoxaiia- ^ on are suspended in 2oo ml 20 ^ ige Satrcmlauee " ^{heated to 0} ° C and slowly 16" ο g ß "Diraethylonineäthy! Chloride. guge «» drips. Nachrüiiren After three hours' can aen cool, s ohiifct elt several times with ether from drives AEEN Ither ¥ b and distilled the Bucks tend under a high vacuum "At a boiling point ton 2O4 ° C and o _t 5 Sorr destillierea 22.5 g of Zp ^ Cfelorphenyl- ^ (ß-dimethylaniinoiithyl) -2 _t 5-diiiydro-1,4-b6rii! OxaBin-3-one about.

10983A / 16SA.

BAD ORiGIHAL

2044119

Example 4

26 _t t » g 2

S / ground in 2oo ml of anhydrous xylene with 4 »7 g liatriuraa & id heated to ssur Bs ond igung dor ta ant development, Therein v / crdon ie _f e g l« Broci ~ 3 «chlori) ropaa added and 5 hours under reflux 'gaicooiit · Ιά dio sieaead® "solution, the solvent is o, 5 g of potassium iodide geg @ b @ a mid, slowly under geriagom overpressure Io s Diiagtli ^ looin eingoloitat, iiach further £ hours Erhitcen is sucked" stripped off and the Büukata & d in Hoa ^ vakuua fractioniort, at a boiling point of 1S4 to ISS ⁰ C and o, l 'forr distill 24 g of 2 «lticmyl-4 ^^^ iffi9thylaainopapopyl) -6« ohlor-2 _t 3 "αυι / θΓθ-1» 4- * ΐ3θΓ ₄ κοχακΐη ~ 3 »οη ale yellow oil that eretasrt after some time and aaim at ö5 ° C

10983-4 / 1 BSA

Claims (1)

204 * 118 Claims ί ^ Process on Hera division basi ^ oh substitute -2,3- ^ Dihydre-l | 4-bineoxazin-3 «one of the" all, * ole-net formula X, where'It ^ is an aliphatic, araliphatic or ao ~ natiaohen Best "The given case nooh further" substituents have tan * H ₂ an alkyl or asylum gritppe, "a halogen", trifluorocjöthyl-i liitro- *, amino, acylamino,! EÖrdr-oxy- odes "allroxyröat odet? aine carboxy "A Ainon Alfey! surest with St'm ß C * atoms and B ^ sinen prlmßarQ" secondary odoe "oyoliaohim Amimfoat. dor iat tied with dom Stiokatoffatom the Alkylenketta _not mean daduroh ^ ^ okonn olohnot ^ daö 114- bGtissoacasiiii — 3 * "one of the general formula ΪΪ, B ₁ and B ₂ mean the above meanings, with reactive esters of arainoalcohols of the general formula ZU, whereby X is an" ealtionable Qo soup, "" B _{# is} a halogen or sulfonic herb and B ^ K have the abovementioned "Bsdsut" ng "n, in alkaline condensation agent at temperatures 2o ° C wnd.l5o ^ö C 2 _f procedure, naefe claim l »dadtireli aefcefflaasaiolm et * daö © as die 2 j3 «Di5jydro-l _f 4 ^ ben20xaain-3 * one ds3? «General ^ "Porael 3B-2saerai" fflit a reafcttonefShige »TerMnduof- * i dev "general formula Ϊ?, where % and A At * meanings Jj & beit and Y a halogen min in · Segenw ^ t basis above rrondensetionnrmittel umnetEt and dsais with aöinen der Ferwöl R« KH _t where 8g the meanings given otsöti bit _t condensed. 3 * terfa? En according to claims 1 and Z _f thereby jf »pkenni soioJm et _ff UnU iaai | the beactlon in an organic solvent or in phase » Herein 1 sheet of Fereeln 109834/16 & A BAD ORiGiNAL