JPS6365671B2 - - Google Patents
Info
- Publication number
- JPS6365671B2 JPS6365671B2 JP13551178A JP13551178A JPS6365671B2 JP S6365671 B2 JPS6365671 B2 JP S6365671B2 JP 13551178 A JP13551178 A JP 13551178A JP 13551178 A JP13551178 A JP 13551178A JP S6365671 B2 JPS6365671 B2 JP S6365671B2
- Authority
- JP
- Japan
- Prior art keywords
- aminal
- pyrrolidine
- benzene
- optically active
- racemic
- 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
- 150000007854 aminals Chemical class 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 7
- -1 2-(N-substituted aminomethyl)pyrrolidine Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YQBLQKZERMAVDO-UHFFFAOYSA-N 2-oxo-2-phenylacetaldehyde;hydrate Chemical compound O.O=CC(=O)C1=CC=CC=C1 YQBLQKZERMAVDO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- KLENTYZJTXGAID-SNVBAGLBSA-N (2s)-2-hydroxy-2-phenylbutanal Chemical compound CC[C@@](O)(C=O)C1=CC=CC=C1 KLENTYZJTXGAID-SNVBAGLBSA-N 0.000 description 2
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- PUMZXCBVHLCWQG-UHFFFAOYSA-N 1-(4-Hydroxyphenyl)-2-aminoethanol hydrochloride Chemical compound [Cl-].[NH3+]CC(O)C1=CC=C(O)C=C1 PUMZXCBVHLCWQG-UHFFFAOYSA-N 0.000 description 1
- UWCWUCKPEYNDNV-UHFFFAOYSA-N 2,6-dimethyl-n-(pyrrolidin-2-ylmethyl)aniline Chemical compound CC1=CC=CC(C)=C1NCC1NCCC1 UWCWUCKPEYNDNV-UHFFFAOYSA-N 0.000 description 1
- LUNGAWJRQUYNRM-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-2-oxoacetaldehyde Chemical compound CC1=CC=C(C(=O)C=O)C(C)=C1 LUNGAWJRQUYNRM-UHFFFAOYSA-N 0.000 description 1
- NGKHHEDLAUNMFD-UHFFFAOYSA-N 2-(4-methylphenyl)-2-oxoacetaldehyde Chemical compound CC1=CC=C(C(=O)C=O)C=C1 NGKHHEDLAUNMFD-UHFFFAOYSA-N 0.000 description 1
- UDHPHCCHADFXHE-JTQLQIEISA-N 2-methoxy-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound COC1=CC=CC=C1NC[C@H]1NCCC1 UDHPHCCHADFXHE-JTQLQIEISA-N 0.000 description 1
- NCFACXDXEKYAOF-UHFFFAOYSA-N 4-methyl-n-(pyrrolidin-2-ylmethyl)aniline Chemical compound C1=CC(C)=CC=C1NCC1NCCC1 NCFACXDXEKYAOF-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- FWTXWYXPXGKVJG-UHFFFAOYSA-N atrolactamide Chemical compound NC(=O)C(O)(C)C1=CC=CC=C1 FWTXWYXPXGKVJG-UHFFFAOYSA-N 0.000 description 1
- 229950011225 atrolactamide Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- MCHWKJRTMPIHRA-UHFFFAOYSA-N n-(pyrrolidin-2-ylmethyl)aniline Chemical compound C1CCNC1CNC1=CC=CC=C1 MCHWKJRTMPIHRA-UHFFFAOYSA-N 0.000 description 1
- SRYXYJQVUDCZIG-UHFFFAOYSA-N n-(pyrrolidin-2-ylmethyl)naphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1NCC1CCCN1 SRYXYJQVUDCZIG-UHFFFAOYSA-N 0.000 description 1
- MCHWKJRTMPIHRA-NSHDSACASA-N n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound C([C@H]1NCCC1)NC1=CC=CC=C1 MCHWKJRTMPIHRA-NSHDSACASA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229940046937 octopamine hydrochloride Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13551178A JPS5562089A (en) | 1978-11-02 | 1978-11-02 | Aminal derivative and its preparation |
| US06/089,356 US4337346A (en) | 1978-11-02 | 1979-10-30 | α-Hydroxyaldehyde and a process for preparing the same |
| EP81108507A EP0048501B1 (en) | 1978-11-02 | 1979-11-02 | Optically active or racemic diazabicyclooctane derivatives |
| EP79302419A EP0011417B1 (en) | 1978-11-02 | 1979-11-02 | Optically active or racemic aminal derivatives, process for preparing same and for converting same to alpha-hydroxyaldehydes |
| DE8181108506T DE2967419D1 (en) | 1978-11-02 | 1979-11-02 | Optically active or racemic alpha-hydroxyaldehydes and benzyl derivatives thereof |
| EP81108506A EP0050351B1 (en) | 1978-11-02 | 1979-11-02 | Optically active or racemic alpha-hydroxyaldehydes and benzyl derivatives thereof |
| DE8181108507T DE2966001D1 (en) | 1978-11-02 | 1979-11-02 | Optically active or racemic diazabicyclooctane derivatives |
| DE7979302419T DE2965322D1 (en) | 1978-11-02 | 1979-11-02 | Optically active or racemic aminal derivatives, process for preparing same and for converting same to alpha-hydroxyaldehydes |
| US06/257,587 US4383122A (en) | 1978-11-02 | 1981-04-27 | Process for preparing α-hydroxyaldehyde |
| US06/457,666 US4584387A (en) | 1978-11-02 | 1983-01-13 | Acyl and ester derivatives of 1,3-diazabicyclo[3,3,0]octane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13551178A JPS5562089A (en) | 1978-11-02 | 1978-11-02 | Aminal derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5562089A JPS5562089A (en) | 1980-05-10 |
| JPS6365671B2 true JPS6365671B2 (ru) | 1988-12-16 |
Family
ID=15153463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13551178A Granted JPS5562089A (en) | 1978-11-02 | 1978-11-02 | Aminal derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5562089A (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH047560U (ru) * | 1990-05-08 | 1992-01-23 |
-
1978
- 1978-11-02 JP JP13551178A patent/JPS5562089A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH047560U (ru) * | 1990-05-08 | 1992-01-23 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5562089A (en) | 1980-05-10 |
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