PL428006A1 - Method of preparing N-(ferrocenylmethyl)-2-amino-1,3-propanediol diester with 4-nitrobenzoic acid - Google Patents
Method of preparing N-(ferrocenylmethyl)-2-amino-1,3-propanediol diester with 4-nitrobenzoic acidInfo
- Publication number
- PL428006A1 PL428006A1 PL428006A PL42800618A PL428006A1 PL 428006 A1 PL428006 A1 PL 428006A1 PL 428006 A PL428006 A PL 428006A PL 42800618 A PL42800618 A PL 42800618A PL 428006 A1 PL428006 A1 PL 428006A1
- Authority
- PL
- Poland
- Prior art keywords
- amino
- propanediol
- ferrocenylmethyl
- reaction
- nitrobenzoic acid
- Prior art date
Links
- -1 N-(ferrocenylmethyl)-2-amino-1,3-propanediol diester Chemical class 0.000 title abstract 4
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 abstract 3
- 238000004440 column chromatography Methods 0.000 abstract 2
- 239000003480 eluent Substances 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 abstract 1
- 150000007824 aliphatic compounds Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000003586 protic polar solvent Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest sposób otrzymywania diestru N-(ferrocenylometylo)-2-amino-1,3-propanodiolu z kwasem 4-nitrobenzoesowym o wzorze 2, który polega na tym, że karboaldehyd ferrocenu poddaje się reakcji z 2-amino-1,3-propanodiolem użytym w ilości 1,2 ekwiwalenta w stosunku do karboaldehydu ferrocenu w rozpuszczalniku protonowym, będącym alkoholem alifatycznym zawierającym co najwyżej trzy atomy węgla, a utworzoną iminę poddaje się redukcji za pomocą tetrahydroboranu użytego w ilości 4 ekwiwalentów w stosunku do karboaldehydu ferrocenu. Reakcję prowadzi się w temperaturze wrzenia rozpuszczalnik a otrzymany N-(ferrocentylometylo)-2-amino-1,3-propanodiol o wzorze 1 wyodrębnia się metodą chromatografii kolumnowej stosując jako eluent mieszaninę chlorek metylenu-alkohol metylowy w stosunku objętościowym 90:10 i poddaje się reakcji z kwasem 4-nitrobenzoesowym użytym w ilości 2 ekwiwalentów w stosunku do N-(ferrocenylometylo)-2-amino-1,3-propanodiolu, w obecności chlorowodorku karbodiimidu alifatycznego zawierającego 8 atomów węgla oraz aromatycznej aminy trzeciorzędowej zawierającej 7 atomów węgla w rozpuszczalniku aprotonowym będącym związkiem alifatycznym zawierającym grupę nitrylową. Reakcję prowadzi się w temperaturze pokojowej a produkt reakcji wyodrębnia się metodą chromatografii kolumnowej stosując jako eluent mieszaninę chlorek metylenu-alkohol metylowy w stosunku objętościowym 90: 10.The subject of the application is a method for the preparation of N- (ferrocenylmethyl) -2-amino-1,3-propanediol diester with 4-nitrobenzoic acid of formula 2, which consists in reacting ferrocene carbaldehyde with 2-amino-1,3- Propanediol used in an amount of 1.2 equivalents to ferrocene carbaldehyde in a protic solvent, which is an aliphatic alcohol with a maximum of three carbon atoms, and the imine formed was reduced with 4 equivalents to the ferrocene carbaldehyde. The reaction is carried out at the reflux temperature of the solvent, and the obtained N- (ferrocentylmethyl) -2-amino-1,3-propanediol of the formula 1 is isolated by column chromatography using a mixture of methylene chloride-methyl alcohol in a volume ratio of 90:10 as eluent and subjected to reaction with 4-nitrobenzoic acid used in an amount of 2 equivalents to N- (ferrocenylmethyl) -2-amino-1,3-propanediol, in the presence of an aliphatic carbodiimide hydrochloride containing 8 carbon atoms and an aromatic tertiary amine containing 7 carbon atoms in an aprotic solvent being an aliphatic compound containing a nitrile group. The reaction was carried out at room temperature and the reaction product was isolated by column chromatography using a mixture of methylene chloride-methyl alcohol in a volume ratio of 90:10 as eluent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL428006A PL238250B1 (en) | 2018-11-30 | 2018-11-30 | Method of preparing N-(ferrocenylmethyl)-2-amino-1,3-propanediol diester with 4-nitrobenzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL428006A PL238250B1 (en) | 2018-11-30 | 2018-11-30 | Method of preparing N-(ferrocenylmethyl)-2-amino-1,3-propanediol diester with 4-nitrobenzoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL428006A1 true PL428006A1 (en) | 2020-06-01 |
| PL238250B1 PL238250B1 (en) | 2021-08-02 |
Family
ID=70855709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL428006A PL238250B1 (en) | 2018-11-30 | 2018-11-30 | Method of preparing N-(ferrocenylmethyl)-2-amino-1,3-propanediol diester with 4-nitrobenzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL238250B1 (en) |
-
2018
- 2018-11-30 PL PL428006A patent/PL238250B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL238250B1 (en) | 2021-08-02 |
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