CA1038406A - Process for recovering phenylalkylamines - Google Patents

Process for recovering phenylalkylamines

Info

Publication number: CA1038406A
Authority: CA; Canada
Prior art keywords: phenyl; process according; mixture; give; propanone
Prior art date: 1973-11-29
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

Application number

CA214,853A

Other languages

English (en)

French (fr)

Other versions

CA214853S (en

Inventor

Henry Najer

Yves R. A. Pascal

Regis Dupont

Don P. R. L. Giudicelli

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Synthelabo SA

Original Assignee

Synthelabo SA

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.)

1973-11-29

Filing date

1974-11-28

Publication date

1978-09-12

1973-11-29 Priority claimed from FR7342537A external-priority patent/FR2253014A1/fr

1974-10-31 Priority claimed from FR7436361A external-priority patent/FR2289487A2/fr

1974-11-28 Application filed by Synthelabo SA filed Critical Synthelabo SA

1978-09-12 Application granted granted Critical

1978-09-12 Publication of CA1038406A publication Critical patent/CA1038406A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 18
239000000203 mixture Substances 0.000 claims abstract description 22
150000001412 amines Chemical class 0.000 claims abstract description 9
230000003287 optical effect Effects 0.000 claims abstract description 9
230000002829 reductive effect Effects 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
230000003647 oxidation Effects 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 4
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 claims 2
HNONSDNCRNUTCT-UHFFFAOYSA-N tiflorex Chemical compound CCNC(C)CC1=CC=CC(SC(F)(F)F)=C1 HNONSDNCRNUTCT-UHFFFAOYSA-N 0.000 claims 2
DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
JPHQCDCEBDRIOL-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]propan-2-one Chemical compound CC(=O)CC1=CC=CC(C(F)(F)F)=C1 JPHQCDCEBDRIOL-UHFFFAOYSA-N 0.000 claims 1
TXDQJVBNHPYFMC-UHFFFAOYSA-N 1-[3-(trifluoromethylsulfanyl)phenyl]propan-2-one Chemical compound CC(=O)CC1=CC=CC(SC(F)(F)F)=C1 TXDQJVBNHPYFMC-UHFFFAOYSA-N 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
230000002891 anorexigenic effect Effects 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
150000007925 phenylethylamine derivatives Chemical class 0.000 description 2
-1 piperidino, morpholino Chemical group 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
229940099594 manganese dioxide Drugs 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000001301 oxygen Chemical group 0.000 description 1
229910052760 oxygen Chemical group 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA214,853A 1973-11-29 1974-11-28 Process for recovering phenylalkylamines Expired CA1038406A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7342537A FR2253014A1 (en)	1973-11-29	1973-11-29	Racemising 1-phenyl-2-aminopropanes - by oxidising to ketone with N-chloro succinimide then reaction with amine
FR7436361A FR2289487A2 (fr)	1974-10-31	1974-10-31	Procede de recuperation de phenylalcoylamines optiquement actives en vue de leur transformation en leurs enanthiomorphes

Publications (1)

Publication Number	Publication Date
CA1038406A true CA1038406A (en)	1978-09-12

Family

ID=26218050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA214,853A Expired CA1038406A (en)	1973-11-29	1974-11-28	Process for recovering phenylalkylamines

Country Status (11)

Country	Link
JP (1)	JPS5331136B2 (ja)
AT (1)	AT335421B (ja)
CA (1)	CA1038406A (ja)
CH (1)	CH603544A5 (ja)
DK (1)	DK616474A (ja)
GB (1)	GB1470110A (ja)
IE (1)	IE40218B1 (ja)
LU (1)	LU71383A1 (ja)
NL (1)	NL7415466A (ja)
NO (1)	NO744291L (ja)
SE (1)	SE7414938L (ja)

1974
- 1974-11-26 IE IE2419/14A patent/IE40218B1/xx unknown
- 1974-11-27 NL NL7415466A patent/NL7415466A/xx not_active Application Discontinuation
- 1974-11-27 DK DK616474A patent/DK616474A/da unknown
- 1974-11-28 AT AT952574A patent/AT335421B/de not_active IP Right Cessation
- 1974-11-28 LU LU71383A patent/LU71383A1/xx unknown
- 1974-11-28 SE SE7414938A patent/SE7414938L/xx unknown
- 1974-11-28 NO NO744291A patent/NO744291L/no unknown
- 1974-11-28 CA CA214,853A patent/CA1038406A/en not_active Expired
- 1974-11-29 JP JP13761874A patent/JPS5331136B2/ja not_active Expired
- 1974-11-29 CH CH1588674A patent/CH603544A5/xx not_active IP Right Cessation
- 1974-11-29 GB GB5182874A patent/GB1470110A/en not_active Expired

Also Published As

Publication number	Publication date
JPS5331136B2 (ja)	1978-08-31
NO744291L (ja)	1975-06-23
AU7579574A (en)	1976-05-27
JPS5088036A (ja)	1975-07-15
NL7415466A (nl)	1975-06-02
AT335421B (de)	1977-03-10
DK616474A (ja)	1975-07-28
LU71383A1 (ja)	1975-08-20
GB1470110A (en)	1977-04-14
IE40218B1 (en)	1979-04-11
SE7414938L (ja)	1975-05-30
CH603544A5 (ja)	1978-08-31
ATA952574A (de)	1976-07-15
IE40218L (en)	1975-05-29

Publication	Publication Date	Title
Carruthers	1986	Some modern methods of organic synthesis
JP3450680B2 (ja)	2003-09-29	パラ−メンタン−３，８−ジオールの製造方法
CA1210770A (en)	1986-09-02	Leukotriene antagonists
CA1137485A (fr)	1982-12-14	Derives de la phenyl-1 (piperidyl-4)-3 propanone-1 utilisables comme medicaments
HU193161B (en)	1987-08-28	Process for preparing new n-alkyl-norscopines
CA1116611A (en)	1982-01-19	Imidazole derivatives exhibiting anticonvulsant activity
EP0522958A1 (fr)	1993-01-13	Procédé de préparation de dérivés de la baccatine III et de la désacétyl-10 baccatine III
US3120551A (en)	1964-02-04	5-(4-biphenylyl)-3-methylvaleric acid and functional derivatives thereof
JP4338401B2 (ja)	2009-10-07	４−フェニル酪酸の合成
HU214054B (en)	1997-12-29	Novel process for preparing formoterol and it's n-alkyl-derivatives
Alberti et al.	1992	Reaction of azoarenes with tributyltin hydride
HU204769B (en)	1992-02-28	New process for producing n-methyl-brackets open p-(trifluoromethyl-phenoxy brackets closed -3-phenylpropaneamine and its acid addition salts
Corey et al.	1975	O, 2-Dilithio derivative of allyl alcohol, a useful synthetic reagent
CA1038406A (en)	1978-09-12	Process for recovering phenylalkylamines
CH615414A5 (ja)	1980-01-31
US3931291A (en)	1976-01-06	Preparation of optically active allethrorone via allethronyl acid phthalate
Strunz et al.	1982	Fittig bislactones in cyclopentenone synthesis: short synthesis of methylenomycin B
JPS60109541A (ja)	1985-06-15	ジアリ−ルインダン−１，３−ジオン，その調製及び使用
AU632117B2 (en)	1992-12-17	Improved process for the preparation of ketone compounds
CA1053687A (en)	1979-05-01	Purification of coumarin and alkylated derivatives of it
FR2475540A1 (fr)	1981-08-14	Ethers basiques de 4-hydroxy-benzophenones, leur preparation et leurs utilisations therapeutiques
EP0351336B1 (fr)	1992-10-28	Procédé de préparation d'hydroxybenzaldéhydes par hydrocarbonylation
EP1349823B1 (en)	2007-11-21	Process for base-promoted condensation reactions and base reagent therefor
US2483347A (en)	1949-09-27	Intermediate products in the production of dialkylamino vitamin a's
BE856317Q (fr)	1977-12-30	Procede de preparation d'acides arylalcanoiques