SU332620A1 - - Google Patents

Info

Publication number

SU332620A1

SU332620A1 SU1420684A SU1420684A SU332620A1 SU 332620 A1 SU332620 A1 SU 332620A1 SU 1420684 A SU1420684 A SU 1420684A SU 1420684 A SU1420684 A SU 1420684A SU 332620 A1 SU332620 A1 SU 332620A1

Authority

SU

USSR - Soviet Union

Prior art keywords

acid

stirred

water

precipitate

hydrogen

Prior art date

Links

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• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• -1 chlorine bromohydride adamantanecarboxylic acid Chemical compound 0.000 description 9
• 239000001257 hydrogen Substances 0.000 description 9
• 229910052739 hydrogen Inorganic materials 0.000 description 9
• 239000000203 mixture Substances 0.000 description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 125000000217 alkyl group Chemical group 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 239000002253 acid Substances 0.000 description 5
• MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 5
• 238000006243 chemical reaction Methods 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 238000000034 method Methods 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• 150000002431 hydrogen Chemical class 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 125000001475 halogen functional group Chemical group 0.000 description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
• 239000012433 hydrogen halide Substances 0.000 description 2
• 229910000039 hydrogen halide Inorganic materials 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 150000004702 methyl esters Chemical class 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
• 229960003424 phenylacetic acid Drugs 0.000 description 2
• 239000003279 phenylacetic acid Substances 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 125000001424 substituent group Chemical group 0.000 description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
• KHMNCHDUSFCTGK-UHFFFAOYSA-N 2-aminophenylacetic acid Chemical compound NC1=CC=CC=C1CC(O)=O KHMNCHDUSFCTGK-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical class C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical class OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
• 125000005518 carboxamido group Chemical group 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 229940052761 dopaminergic adamantane derivative Drugs 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 238000011835 investigation Methods 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• HJXXEMDHWOGUKY-UHFFFAOYSA-N methyl 2-(2-amino-4-methylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(C)C=C1N HJXXEMDHWOGUKY-UHFFFAOYSA-N 0.000 description 1
• CXEYRQHGCXGOKC-UHFFFAOYSA-N methyl 2-(2-aminophenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=CC=C1N CXEYRQHGCXGOKC-UHFFFAOYSA-N 0.000 description 1
• CIOZXSGIYJWVGZ-UHFFFAOYSA-N methyl 2-[2-amino-4-(trifluoromethyl)phenyl]hexanoate Chemical compound NC1=C(C=CC(=C1)C(F)(F)F)C(C(=O)OC)CCCC CIOZXSGIYJWVGZ-UHFFFAOYSA-N 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 230000001766 physiological effect Effects 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 239000013049 sediment Substances 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 238000000638 solvent extraction Methods 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1