GB580392A - Manufacture of piperidino-ethanol ester of di-n-butylacetic acid - Google Patents
Manufacture of piperidino-ethanol ester of di-n-butylacetic acidInfo
- Publication number
- GB580392A GB580392A GB16252/44A GB1625244A GB580392A GB 580392 A GB580392 A GB 580392A GB 16252/44 A GB16252/44 A GB 16252/44A GB 1625244 A GB1625244 A GB 1625244A GB 580392 A GB580392 A GB 580392A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperidino
- ester
- acetic acid
- halogen
- ethanol
- 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
- KQYRYPXQPKPVSP-UHFFFAOYSA-N 2-butylhexanoic acid Chemical compound CCCCC(C(O)=O)CCCC KQYRYPXQPKPVSP-UHFFFAOYSA-N 0.000 title abstract 6
- -1 piperidino-ethanol ester Chemical class 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- MADORZDTLHDDEN-UHFFFAOYSA-N 1-piperidin-1-ylethanol Chemical compound CC(O)N1CCCCC1 MADORZDTLHDDEN-UHFFFAOYSA-N 0.000 abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 4
- 239000005977 Ethylene Substances 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- HXGZVSNYYXBNIT-UHFFFAOYSA-N 2-butylhexanoyl chloride Chemical compound CCCCC(C(Cl)=O)CCCC HXGZVSNYYXBNIT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The piperidino-ethanol ester of di-n-butyl acetic acid which has pronounced cramp-relieving properties, may be prepared according to the hereinafter described methods. The halides, esters or anhydride of di-n-butyl acetic acid may be reacted in the presence of absence of condensation agents with piperidino-ethanol, or salts of the acid may be reacted with reactive esters of piperidino-ethanol, for example, esters with halogen hydracids or aryl sulphonic acids. A further method consists in converting the di-n-butyl acetic acid into its halogen-ethyl ester and reacting the latter with piperidine. The halogen ethyl ester may be prepared by reacting the acid, its halides, esters or anhydride with an ethylene halogen hydrin in the presence or absence of condensation agents, or by reacting salts of the acid with ethylene dihalide or ethylene halogen hydrin and replacing the hydroxyl group present in the compounds obtained by the latter method by halogen. The basic ester is water soluble in the form of its salts with inorganic or organic acids. In examples: (1) di-n-butyl acetic acid chloride is reacted with piperidino ethanol to give the desired ester; (2) di-n-butyl acetic acid chloride is reacted with ethylene chlorhydrin in the presence of pyridine and the b -chloroethyl ester of the dibutyl acetic acid so obtained is reacted with piperidine to give the desired piperidineethyl ester. The Specification as open to inspection under Sect. 91 includes also the preparation of piperidino ester of di-n-butyl acetic acid by reacting the acid with reactive esters of piperidino ethanol in the presence or not of acid binding agents. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH580392X | 1943-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB580392A true GB580392A (en) | 1946-09-05 |
Family
ID=4521466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16252/44A Expired GB580392A (en) | 1943-08-04 | 1944-08-28 | Manufacture of piperidino-ethanol ester of di-n-butylacetic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB580392A (en) |
-
1944
- 1944-08-28 GB GB16252/44A patent/GB580392A/en not_active Expired
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