JPS61260074A - １−アミジノ−４−ホルミルピペラジン類の製造法 - Google Patents
１−アミジノ−４−ホルミルピペラジン類の製造法Info
- Publication number
- JPS61260074A JPS61260074A JP60101878A JP10187885A JPS61260074A JP S61260074 A JPS61260074 A JP S61260074A JP 60101878 A JP60101878 A JP 60101878A JP 10187885 A JP10187885 A JP 10187885A JP S61260074 A JPS61260074 A JP S61260074A
- Authority
- JP
- Japan
- Prior art keywords
- mineral acid
- formylpiperazine
- formula
- cyanamide
- compound
- 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.)
- Granted
Links
- PEQMIPITRYDCFN-UHFFFAOYSA-N 4-formylpiperazine-1-carboximidamide Chemical compound NC(=N)N1CCN(C=O)CC1 PEQMIPITRYDCFN-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000002253 acid Substances 0.000 claims abstract description 22
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 22
- 239000011707 mineral Substances 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 18
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 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
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- -1 methanol or ethanol Chemical class 0.000 description 2
- BHCYHIHXZYQUHZ-UHFFFAOYSA-N piperazine-1,4-dicarboximidamide Chemical class NC(=N)N1CCN(C(N)=N)CC1 BHCYHIHXZYQUHZ-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- SRDWJJXSQNOJLZ-UHFFFAOYSA-N 2,5-dimethylpiperazine-1-carbaldehyde Chemical compound CC1CN(C=O)C(C)CN1 SRDWJJXSQNOJLZ-UHFFFAOYSA-N 0.000 description 1
- QOIJPNNTPPTGMY-UHFFFAOYSA-N 2-methylpiperazine-1-carbaldehyde Chemical compound CC1CNCCN1C=O QOIJPNNTPPTGMY-UHFFFAOYSA-N 0.000 description 1
- ODOBIPKDHNFKTO-UHFFFAOYSA-N CCC1CN(C=O)CCN1 Chemical compound CCC1CN(C=O)CCN1 ODOBIPKDHNFKTO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-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
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012971 dimethylpiperazine Substances 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
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- ZIPLUEXSCPLCEI-UHFFFAOYSA-N iminomethylideneazanide Chemical group [NH-]C#N ZIPLUEXSCPLCEI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60101878A JPS61260074A (ja) | 1985-05-13 | 1985-05-13 | １−アミジノ−４−ホルミルピペラジン類の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60101878A JPS61260074A (ja) | 1985-05-13 | 1985-05-13 | １−アミジノ−４−ホルミルピペラジン類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61260074A true JPS61260074A (ja) | 1986-11-18 |
| JPH0578550B2 JPH0578550B2 (enrdf_load_stackoverflow) | 1993-10-29 |
Family
ID=14312208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60101878A Granted JPS61260074A (ja) | 1985-05-13 | 1985-05-13 | １−アミジノ−４−ホルミルピペラジン類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61260074A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5432178A (en) * | 1992-09-18 | 1995-07-11 | Ono Pharmaceutical Co., Ltd. | Amidinophenol derivatives |
-
1985
- 1985-05-13 JP JP60101878A patent/JPS61260074A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5432178A (en) * | 1992-09-18 | 1995-07-11 | Ono Pharmaceutical Co., Ltd. | Amidinophenol derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0578550B2 (enrdf_load_stackoverflow) | 1993-10-29 |
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