AT392782B - Verfahren zur herstellung von alpha-(p-tent.- butylphenyl)-4-(hydroxydiphenylmethyl)-1- piperidinobutanol - Google Patents

Verfahren zur herstellung von alpha-(p-tent.- butylphenyl)-4-(hydroxydiphenylmethyl)-1- piperidinobutanol Download PDF

Info

Publication number: AT392782B
Authority: AT; Austria
Prior art keywords: tert; butylbenzoyl; propionic acid; added; mixture
Prior art date: 1985-09-27

Application number

AT257686A

Other languages

German (de)

English (en)

Other versions

ATA257686A (de

Inventor

Fulvio Benigni

Original Assignee

Ind Chimica Srl

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.)

1985-09-27

Filing date

1986-09-26

Publication date

1991-06-10

1986-09-26 Application filed by Ind Chimica Srl filed Critical Ind Chimica Srl

1990-11-15 Publication of ATA257686A publication Critical patent/ATA257686A/de

1991-06-10 Application granted granted Critical

1991-06-10 Publication of AT392782B publication Critical patent/AT392782B/de

Links

238000000034 method Methods 0.000 title claims description 12
230000008569 process Effects 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 3
SLPPKRDJWNQGAW-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-5,5-diphenyl-1-piperidin-1-ylpentane-1,5-diol Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)(N1CCCCC1)CCCC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 SLPPKRDJWNQGAW-UHFFFAOYSA-N 0.000 title abstract 2
XJHBTHNAMOUNRQ-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-4-oxobutanoic acid Chemical class CC(C)(C)C1=CC=C(C(=O)CCC(O)=O)C=C1 XJHBTHNAMOUNRQ-UHFFFAOYSA-N 0.000 claims abstract description 8
239000012280 lithium aluminium hydride Substances 0.000 claims abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
-1 p-tert-butylphenyl Chemical group 0.000 claims description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
239000000047 product Substances 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
239000012043 crude product Substances 0.000 claims description 4
238000002329 infrared spectrum Methods 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
238000004458 analytical method Methods 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
229940014800 succinic anhydride Drugs 0.000 claims description 3
238000004809 thin layer chromatography Methods 0.000 claims description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
239000003480 eluent Substances 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
239000000155 melt Substances 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
239000000741 silica gel Substances 0.000 claims description 2
229910002027 silica gel Inorganic materials 0.000 claims description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
230000008034 disappearance Effects 0.000 claims 1
238000001035 drying Methods 0.000 claims 1
238000003756 stirring Methods 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
230000003266 anti-allergic effect Effects 0.000 abstract 1
230000001387 anti-histamine Effects 0.000 abstract 1
239000000739 antihistaminic agent Substances 0.000 abstract 1
ZMISODWVFHHWNR-UHFFFAOYSA-N diphenyl(4-piperidinyl)methanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1CCNCC1 ZMISODWVFHHWNR-UHFFFAOYSA-N 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 4
239000012265 solid product Substances 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229960000351 terfenadine Drugs 0.000 description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
PPCDNROOWUPPBJ-UHFFFAOYSA-N 3-(2-tert-butylphenyl)-2-methyl-3-oxopropanoic acid Chemical compound C(C)(C)(C)C1=C(C(=O)C(C(=O)O)C)C=CC=C1 PPCDNROOWUPPBJ-UHFFFAOYSA-N 0.000 description 1
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
230000003670 easy-to-clean Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 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
125000000468 ketone group Chemical group 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Landscapes

Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

AT257686A 1985-09-27 1986-09-26 Verfahren zur herstellung von alpha-(p-tent.- butylphenyl)-4-(hydroxydiphenylmethyl)-1- piperidinobutanol AT392782B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT48596/85A IT1200123B (it)	1985-09-27	1985-09-27	Procedimento per la preparazione di alfa-(p-terbutilfenil)-4-(idrossidifenilmetil)-1-piperidinobutanolo

Publications (2)

Publication Number	Publication Date
ATA257686A ATA257686A (de)	1990-11-15
AT392782B true AT392782B (de)	1991-06-10

Family

ID=11267539

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT257686A AT392782B (de)	1985-09-27	1986-09-26	Verfahren zur herstellung von alpha-(p-tent.- butylphenyl)-4-(hydroxydiphenylmethyl)-1- piperidinobutanol

Country Status (5)

Country	Link
AT (1)	AT392782B (it)
ES (1)	ES8700849A1 (it)
IT (1)	IT1200123B (it)
SU (1)	SU1486058A3 (it)
YU (1)	YU44293B (it)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2002102776A1 (en) *	2001-06-15	2002-12-27	Aventis Pharma Deutschland Gmbh	Process for the production of the piperidine derivative fexofenadine

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2681861B1 (fr) *	1991-10-01	1995-06-09	Isochem Sa	Procede de preparation d'une forme polymorphique de la terfenadine, a point de fusion eleve, d'une plus grande purete et produit obtenu.
EP1026147B1 (en)	1993-06-24	2003-11-19	Albany Molecular Research, Inc.	Compounds useful as intermediates in the production of piperidine derivatives
US20020007068A1 (en)	1999-07-16	2002-01-17	D'ambra Thomas E.	Piperidine derivatives and process for their production

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2303306A1 (de) *	1972-01-28	1973-08-02	Richardson Merrell Inc	Alpha-aryl-4-substituierte piperidinoalkanol-derivate und verfahren zu deren herstellung

1985
- 1985-09-27 IT IT48596/85A patent/IT1200123B/it active
- 1985-11-05 ES ES548555A patent/ES8700849A1/es not_active Expired
1986
- 1986-07-02 YU YU116886A patent/YU44293B/xx unknown
- 1986-09-26 AT AT257686A patent/AT392782B/de not_active IP Right Cessation
- 1986-09-26 SU SU864028203A patent/SU1486058A3/ru active

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2303306A1 (de) *	1972-01-28	1973-08-02	Richardson Merrell Inc	Alpha-aryl-4-substituierte piperidinoalkanol-derivate und verfahren zu deren herstellung

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2002102776A1 (en) *	2001-06-15	2002-12-27	Aventis Pharma Deutschland Gmbh	Process for the production of the piperidine derivative fexofenadine
US6743941B2 (en)	2001-06-15	2004-06-01	Aventis Pharma Deutschland Gmbh	Process for the production of piperidine derivatives
US7235665B2 (en)	2001-06-15	2007-06-26	Sanofi-Aventis Deutschland Gmbh	Process for the production of piperidine derivatives
AU2002320847B2 (en) *	2001-06-15	2007-09-20	Sanofi-Aventis Deutschland Gmbh	Process for the production of the piperidine derivative fexofenadine

Also Published As

Publication number	Publication date
IT8548596A0 (it)	1985-09-27
YU44293B (en)	1990-04-30
ES548555A0 (es)	1986-11-16
SU1486058A3 (ru)	1989-06-07
ES8700849A1 (es)	1986-11-16
YU116886A (en)	1987-12-31
ATA257686A (de)	1990-11-15
IT1200123B (it)	1989-01-05

Legal Events

Date	Code	Title	Description
1995-08-15	ELJ	Ceased due to non-payment of the annual fee

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