| Identification | Back Directory | [Name]
ethyl 4-[(2-amino-4-chlorophenyl)amino]piperidine-1-carboxylate | [CAS]
53786-45-1 | [Synonyms]
Einecs 258-775-8
Domperidone Impurity 8
Domperidone Impurity 2
ethyl 4-((2-amino-4-chlorophenyl)
ETHYL 4-(2-AMINO-4-CHLOROANILINO)PIPERIDINE-1-CARBOXYLATE
ethyl 4-[(2-amino-4-chlorophenyl)amino]piperidine-1-carboxylate
4-[(2-Amino-4-chlorophenyl)amino]-1-piperidinecarboxylic acid ethyl ester
1-PIPERIDINECARBOXYLIC ACID,4-[(2-AMINO-4-CHLOROPHENYL)AMINO]-,ETHYL ESTER | [EINECS(EC#)]
258-775-8 | [Molecular Formula]
C14H20ClN3O2 | [MDL Number]
MFCD03931057 | [MOL File]
53786-45-1.mol | [Molecular Weight]
297.78 |
| Chemical Properties | Back Directory | [Boiling point ]
475.6±45.0 °C(Predicted) | [density ]
1.290±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [pka]
4.70±0.11(Predicted) | [InChI]
InChI=1S/C14H20ClN3O2/c1-2-20-14(19)18-7-5-11(6-8-18)17-13-4-3-10(15)9-12(13)16/h3-4,9,11,17H,2,5-8,16H2,1H3 | [InChIKey]
PPCPQDDCMQRJLS-UHFFFAOYSA-N | [SMILES]
N1(C(OCC)=O)CCC(NC2=CC=C(Cl)C=C2N)CC1 |
| Hazard Information | Back Directory | [Uses]
Ethyl 4-((2-Amino-4-chlorophenyl)amino)piperidine-1-carboxylate is an impurity of Domperidone(D531100); a novel peripheral dopamine receptor antagonist that does not cross the blood-brain barrier; anti-emetic. Domperidone(Motilium) is a dopamine blocker and an antidopaminergic reagent. | [Synthesis]
2. 1.34 kg of the crude product (domperidone impurity 7) obtained in the first step was dissolved in a solvent mixture of 15 L of methanol and 15 L of tetrahydrofuran with 1.3 L of water. Subsequently, zinc powder and 1.1 kg of ammonium chloride were added and the reaction was carried out at 25 °C for 5 hours. After completion of the reaction, the zinc powder was removed by filtration. Methanol and tetrahydrofuran were recovered by concentration under reduced pressure. The residue was dissolved in 15 L of ethyl acetate and the organic phase was washed with 15 L of water. The organic phase was recrystallized by adding 1 kg of ethyl acetate and 3 kg of petroleum ether to give 1.06 kg of an off-white solid, domperidone intermediate (DP-2), with 99% purity and 88% yield. | [References]
[1] Journal of Medicinal Chemistry, 1987, vol. 30, # 5, p. 814 - 820
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 5052 - 5056
[3] Patent: US4470989, 1984, A
[4] Patent: CN108358832, 2018, A. Location in patent: Paragraph 0007; 0020; 0023; 0029; 0033; 0037 |
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| Company Name: |
Struchem Co., Ltd.
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0512-63009836 18994340901 |
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www.beidapharma.com |
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