SI9010634B - Nov postopek za sintezo N-metil-3,4-dimetoksifeniletilamina - Google Patents

Nov postopek za sintezo N-metil-3,4-dimetoksifeniletilamina Download PDF

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Publication number
SI9010634B
SI9010634B SI9010634A SI9010634A SI9010634B SI 9010634 B SI9010634 B SI 9010634B SI 9010634 A SI9010634 A SI 9010634A SI 9010634 A SI9010634 A SI 9010634A SI 9010634 B SI9010634 B SI 9010634B
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SI
Slovenia
Prior art keywords
formula
haco
process according
hours
temperature
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SI9010634A
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English (en)
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SI9010634A (en
Inventor
Vincenzo Cannata
Giancarlo Tamerlani
Graziano Zagnoni
Original Assignee
Alfa Chemicals Italiana S.P.A.
Priority date (The priority date 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 date listed.)
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Publication date
Application filed by Alfa Chemicals Italiana S.P.A. filed Critical Alfa Chemicals Italiana S.P.A.
Publication of SI9010634A publication Critical patent/SI9010634A/sl
Publication of SI9010634B publication Critical patent/SI9010634B/sl

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/50—Ethers of hydroxy amines of undetermined structure, e.g. obtained by reactions of epoxides with hydroxy amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (7)

  1. - 13 - PATENTNI ZAHTEVKI 1. Nov kemijski postopek za sintezo N-metil-3,11-dimetoksifeniletilamina s formulo HaCO HaCO
    CHa-CHa-NH-CHa I j označen s tem, da a) presnovimo 3,4-dimetoksibenzaldehid s formulo .CHO HaCO II HaCO z ος-haloestrora s formulo x-ch2-coor VI , kjer X pomeni atom halogena in R pomeni raven ali razvejen alkilni radikal, ki vsebuje 1 do 6 ogljikovih atomov, v prisot nosti alkalnega sredstva, izbranega med alkoholatom alkalijske kovine s formulo R^* Me+ VII kjer Me+ pomeni kation alkalijske kovine in je R^ raven ali razvejen alkilni radikal, ki vsebuje 1 do 6 ogljikovih atomov, - 14 - natrijevim amidom ali natrijevim hidridom, v danem primeru v prisotnosti topila, izbranega med aromatskim ogljikovodikom in ravnim ali razvejenim alkoholom, ki vsebuje 1 do 6 ogljikovih atomov, ali njunih zmesi, v času med . 1 in 6 ur, pri temperaturi med 0°C in 40°C, b) dobljeni ester glicidne kisline s formulo
    HaCO kjer ima R gornji pomen, alkalno hidroliziramo pri temperaturi med 10°C in 40°C v času med . 6 in . 24 ur , da dobimo alkalijsko sol epoksi kisline s formulo HaCO HaCO
    ch-ch-ooo-
    Me- IV ) kjer ima Me gornji pomen, c) dekarboksiliramo spojino s formulo IV v kislem mediju pri temperaturi med 10°C in . 40°C v času med 1 in 8 ur, da dobimo 3,4-dimetoksibenzenacetaldehid s formulo HaCO CHa-CHO - 15 - d) obdelamo ta aldehid 3 formulo V najprej z raonometilaminom pri temperaturi med -10°C in . 4Q°C v času med 1 in 6 ur in nato z natrijevim borohidridom pri temperaturi med -10°C in 80°C v času med 2 in 8 ur, da dobimo N-metil-3»4-dimetoksifeniletilamin s formulo I.
  2. 2. Postopek po zahtevku 1, označen s tem, da uporabimo za vsak mol 3»4-dimetoksibenzaldehida 1 do .4 mole cx.-haloestra s formulo VI in 1 do 4 mole baze, izbrane med alkalijskim alkoholatom s formulo VII, natrijevim amidom in natrijevim hidridom.
  3. 3- Postopek po zahtevku 1, označen s tem, da izberemo cX.-haloe3ter s formulo VI med metil kloroacetatora, etil kloro-acetatom in 2-butil kloroacetatom.
  4. 4. Postopek po zahtevku 1, označen s tem, da izberemo alkoholat s formulo VII med natrijevim metoksidom, kalijevim 2-butoksidom, natrijevim 2-butoksidom, kalijevim terc-butoksidom in kalijevim n-propoksidom.
  5. 5. Postopek po zahtevku 1, označen s tem, da je topilo, ki ga uporabljamo, da dobimo ester glicidne kisline s formulo III, 2-butanol.
  6. 6. Postopek po zahtevku 1, označen s tem, da se vrši dekarboksiliranje v prisotnosti monokalijevega fosfata.
  7. 7. Postopek po zahtevku 1, označen s tem, da uporabimo 1 do 6 molskih ekvivalentov monometilamina v vodni raztopini. Za 24026-Χ-97-mn Alfa Chemicals Italiana S.p.A.:
    .0. 14
SI9010634A 1989-03-31 1990-03-29 Nov postopek za sintezo N-metil-3,4-dimetoksifeniletilamina SI9010634B (sl)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT8919959A IT1229214B (it) 1989-03-31 1989-03-31 Processo per la sintesi della n metil 3,4 dimetossifeniletilamina
YU63490A YU48167B (sh) 1989-03-31 1990-03-29 Nov postupak za sintezu n-metil-3,4-dimetoksifeniletilamina

Publications (2)

Publication Number Publication Date
SI9010634A SI9010634A (en) 1997-08-31
SI9010634B true SI9010634B (sl) 1998-06-30

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ID=11162654

Family Applications (1)

Application Number Title Priority Date Filing Date
SI9010634A SI9010634B (sl) 1989-03-31 1990-03-29 Nov postopek za sintezo N-metil-3,4-dimetoksifeniletilamina

Country Status (25)

Country Link
US (1) US5057624A (sl)
EP (1) EP0389876B1 (sl)
JP (1) JPH06102636B2 (sl)
KR (1) KR940011899B1 (sl)
AR (1) AR245930A1 (sl)
AT (1) ATE92467T1 (sl)
AU (1) AU627561B2 (sl)
CA (1) CA2013080C (sl)
DD (1) DD293109A5 (sl)
DE (1) DE69002500T2 (sl)
DK (1) DK0389876T3 (sl)
ES (1) ES2058644T3 (sl)
FI (1) FI102370B (sl)
HR (1) HRP940599B1 (sl)
HU (1) HU209947B (sl)
IE (1) IE63954B1 (sl)
IL (1) IL93762A (sl)
IT (1) IT1229214B (sl)
NO (1) NO170149C (sl)
NZ (1) NZ232975A (sl)
PL (1) PL162349B1 (sl)
PT (1) PT93598B (sl)
SI (1) SI9010634B (sl)
YU (1) YU48167B (sl)
ZA (1) ZA902003B (sl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR19990014830A (ko) * 1995-05-17 1999-02-25 카르크 Ｎ-메틸-2-(3,4-디메톡시페닐)에틸아민의 제조 방법
CN101580460B (zh) * 2009-05-26 2012-05-23 台州市知青化工有限公司 一种3，4-二羟基苯乙醇的合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3894051A (en) * 1973-07-05 1975-07-08 Colgate Palmolive Co N-methylenedioxyphenylalkyl)-{62 -(alkyl)-disubstituted phenethylamines
US3997608A (en) * 1973-07-05 1976-12-14 Richardson-Merrell Inc. N-substituted-dihydroxyphenethylamines
DE3338681A1 (de) * 1983-10-25 1985-05-09 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von n-methylhomoveratrylamin
GB8603765D0 (en) * 1986-02-15 1986-03-19 Beecham Wuelfung Gmbh & Co Kg Compounds
IT1215409B (it) * 1987-04-08 1990-02-08 Alfa Chem Ital Processo per la sintesi dell'alfa-(1-metiletil)-3,4-dimetossibenzeneacetonitrile.

Also Published As

Publication number Publication date
DE69002500T2 (de) 1994-01-13
JPH06102636B2 (ja) 1994-12-14
KR900014310A (ko) 1990-10-23
HRP940599B1 (en) 1998-04-30
NO901454D0 (no) 1990-03-30
NO170149C (no) 1992-09-16
AR245930A1 (es) 1994-03-30
EP0389876B1 (en) 1993-08-04
ES2058644T3 (es) 1994-11-01
HUT53865A (en) 1990-12-28
EP0389876A1 (en) 1990-10-03
PT93598A (pt) 1990-11-20
FI102370B1 (fi) 1998-11-30
NZ232975A (en) 1991-11-26
ATE92467T1 (de) 1993-08-15
IT8919959A0 (it) 1989-03-31
CA2013080C (en) 1997-07-22
HU902025D0 (en) 1990-07-28
YU63490A (en) 1991-10-31
CA2013080A1 (en) 1990-09-30
SI9010634A (en) 1997-08-31
IE901171L (en) 1990-09-30
NO901454L (no) 1990-10-01
HU209947B (en) 1994-12-28
PL162349B1 (pl) 1993-10-30
AU627561B2 (en) 1992-08-27
DD293109A5 (de) 1991-08-22
NO170149B (no) 1992-06-09
DE69002500D1 (de) 1993-09-09
JPH02289539A (ja) 1990-11-29
ZA902003B (en) 1990-12-28
PT93598B (pt) 1996-03-29
FI901611A0 (fi) 1990-03-30
US5057624A (en) 1991-10-15
HRP940599A2 (en) 1997-06-30
DK0389876T3 (da) 1993-09-27
KR940011899B1 (ko) 1994-12-27
IL93762A (en) 1994-07-31
IT1229214B (it) 1991-07-25
AU5247090A (en) 1990-10-04
IE63954B1 (en) 1995-06-28
IL93762A0 (en) 1990-12-23
YU48167B (sh) 1997-07-31
FI102370B (fi) 1998-11-30

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