CA1129424A - Synthese d'haloperidole - Google Patents
Synthese d'haloperidoleInfo
- Publication number
- CA1129424A CA1129424A CA326,038A CA326038A CA1129424A CA 1129424 A CA1129424 A CA 1129424A CA 326038 A CA326038 A CA 326038A CA 1129424 A CA1129424 A CA 1129424A
- Authority
- CA
- Canada
- Prior art keywords
- haloperidol
- compound
- formula
- preparing
- isolating
- Prior art date
- 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
Links
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 229960003878 haloperidol Drugs 0.000 title claims abstract description 17
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Chemical group 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
- LZAYOZUFUAMFLD-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxypiperidine Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCNCC1 LZAYOZUFUAMFLD-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000003637 basic solution Substances 0.000 claims abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- HXAOUYGZEOZTJO-UHFFFAOYSA-N 4-chloro-1-(4-fluorophenyl)butan-1-one Chemical compound FC1=CC=C(C(=O)CCCCl)C=C1 HXAOUYGZEOZTJO-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002084 enol ethers Chemical class 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- PXAJMBHRLGKPQV-UHFFFAOYSA-N 4-(4-chlorophenyl)piperidin-4-ol;hydron;chloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(O)CCNCC1 PXAJMBHRLGKPQV-UHFFFAOYSA-N 0.000 description 1
- JMRYYMBDXNZQMH-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one;hydrochloride Chemical compound Cl.C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 JMRYYMBDXNZQMH-UHFFFAOYSA-N 0.000 description 1
- RKNNOFFPYRLSNO-UHFFFAOYSA-N 4-fluoro-1-phenylbutan-1-one Chemical compound FCCCC(=O)C1=CC=CC=C1 RKNNOFFPYRLSNO-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1787—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings and having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15642/78A GB1596874A (en) | 1978-04-20 | 1978-04-20 | Synthesis of haloperidol |
| GB15642/78 | 1978-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1129424A true CA1129424A (fr) | 1982-08-10 |
Family
ID=10062830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA326,038A Expired CA1129424A (fr) | 1978-04-20 | 1979-04-20 | Synthese d'haloperidole |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS54145675A (fr) |
| BE (1) | BE875699A (fr) |
| CA (1) | CA1129424A (fr) |
| DE (1) | DE2915596A1 (fr) |
| FR (1) | FR2423470A1 (fr) |
| GB (1) | GB1596874A (fr) |
| IT (1) | IT1120411B (fr) |
| NL (1) | NL7903086A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61250793A (ja) * | 1985-04-30 | 1986-11-07 | Canon Inc | 文字認識装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5653534B2 (fr) * | 1973-10-25 | 1981-12-19 |
-
1978
- 1978-04-20 GB GB15642/78A patent/GB1596874A/en not_active Expired
-
1979
- 1979-04-18 DE DE19792915596 patent/DE2915596A1/de not_active Withdrawn
- 1979-04-18 FR FR7909717A patent/FR2423470A1/fr active Granted
- 1979-04-19 BE BE0/194702A patent/BE875699A/fr not_active IP Right Cessation
- 1979-04-19 NL NL7903086A patent/NL7903086A/xx not_active Application Discontinuation
- 1979-04-19 IT IT48783/79A patent/IT1120411B/it active
- 1979-04-20 CA CA326,038A patent/CA1129424A/fr not_active Expired
- 1979-04-20 JP JP4886879A patent/JPS54145675A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54145675A (en) | 1979-11-14 |
| BE875699A (fr) | 1979-08-16 |
| IT1120411B (it) | 1986-03-26 |
| GB1596874A (en) | 1981-09-03 |
| FR2423470B1 (fr) | 1983-11-18 |
| FR2423470A1 (fr) | 1979-11-16 |
| DE2915596A1 (de) | 1979-10-31 |
| NL7903086A (nl) | 1979-10-23 |
| IT7948783A0 (it) | 1979-04-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |