JPH0578549B2 - - Google Patents
Info
- Publication number
- JPH0578549B2 JPH0578549B2 JP60101877A JP10187785A JPH0578549B2 JP H0578549 B2 JPH0578549 B2 JP H0578549B2 JP 60101877 A JP60101877 A JP 60101877A JP 10187785 A JP10187785 A JP 10187785A JP H0578549 B2 JPH0578549 B2 JP H0578549B2
- Authority
- JP
- Japan
- Prior art keywords
- amidino
- formylpiperazines
- mineral acid
- reaction
- present
- 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 - Lifetime
Links
- 150000003839 salts Chemical class 0.000 claims description 24
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 17
- 239000011707 mineral Substances 0.000 claims description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- PEQMIPITRYDCFN-UHFFFAOYSA-N 4-formylpiperazine-1-carboximidamide Chemical class NC(=N)N1CCN(C=O)CC1 PEQMIPITRYDCFN-UHFFFAOYSA-N 0.000 claims description 10
- ZTWBXCGKRKUYSY-UHFFFAOYSA-N piperazine-1-carboximidamide Chemical class NC(=N)N1CCNCC1 ZTWBXCGKRKUYSY-UHFFFAOYSA-N 0.000 claims description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- -1 1-amidino-2,6-dimethylpiperazine Chemical compound 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 2
- OJPUGXJCTUOTHU-UHFFFAOYSA-N 2,5-dimethylpiperazine-1-carboximidamide Chemical compound CC1CN(C(N)=N)C(C)CN1 OJPUGXJCTUOTHU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JQCOLDBPPJXYQL-UHFFFAOYSA-N 2-methylpiperazine-1-carboximidamide Chemical compound CC1CNCCN1C(N)=N JQCOLDBPPJXYQL-UHFFFAOYSA-N 0.000 description 1
- RPZVORJAHQLBNU-UHFFFAOYSA-N 3-ethylpiperazine-1-carboximidamide Chemical compound C(N)(=N)N1CC(NCC1)CC RPZVORJAHQLBNU-UHFFFAOYSA-N 0.000 description 1
- FAIHBKPJKQQTOT-UHFFFAOYSA-N 3-methylpiperazine-1-carboximidamide Chemical compound CC1CN(C(N)=N)CCN1 FAIHBKPJKQQTOT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60101877A JPS61260073A (ja) | 1985-05-13 | 1985-05-13 | １−アミジノ−４−ホルミルピペラジン類を製造する方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60101877A JPS61260073A (ja) | 1985-05-13 | 1985-05-13 | １−アミジノ−４−ホルミルピペラジン類を製造する方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61260073A JPS61260073A (ja) | 1986-11-18 |
| JPH0578549B2 true JPH0578549B2 (enrdf_load_stackoverflow) | 1993-10-29 |
Family
ID=14312187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60101877A Granted JPS61260073A (ja) | 1985-05-13 | 1985-05-13 | １−アミジノ−４−ホルミルピペラジン類を製造する方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61260073A (enrdf_load_stackoverflow) |
-
1985
- 1985-05-13 JP JP60101877A patent/JPS61260073A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61260073A (ja) | 1986-11-18 |