BAMIPINE

BAMIPINE Basic information
Product Name:BAMIPINE
Synonyms:Taumidrin;BAMIPINE;4-(N-Benzylanilino)-1-methylpiperidine;4-(n-benzyl-n-phenylamino)-1-methyl-piperidin;4-(N-Benzyl-N-phenylamino)-1-methylpiperidine;4-Piperidinamine, 1-methyl-N-phenyl-N-(phenylmethyl)-;N-Benzyl-1-methyl-N-phenyl-4-piperidinamine;N-Phenyl-N-benzyl-4-amino-1-methyl-piperidine
CAS:4945-47-5
MF:C19H24N2
MW:280.41
EINECS:225-587-2
Product Categories:
Mol File:4945-47-5.mol
BAMIPINE Structure
BAMIPINE Chemical Properties
Melting point 115°
Boiling point 413.12°C (rough estimate)
density 0.9608 (rough estimate)
refractive index 1.8676 (estimate)
pkapKa 3.34±0.04 (H2O t unde?ned I=0.30(NaCl)) (Uncertain);8.04±0.11(H2O t unde?ned I=0.30(NaCl)) (Uncertain)
Safety Information
MSDS Information
BAMIPINE Usage And Synthesis
OriginatorBamipine,Pharm Chemical
UsesBamipine is an antihistamine that has anticholinergic properties. It is also a reagent for dopamine D3 receptor ligands based on scaffolds of biogenic amine GPCR (G protein-coupled receptor) ligands.
DefinitionChEBI: Bamipine is an aromatic amine.
Manufacturing Process80 g of 1-methyl-piperidone-4 and 70 g of aniline are boiled, using a water separator in 350 ml of toluene to which several drops of glacial acetic acid have been added, until the theoretical quantity of water (12.7 ml) has separated out. The toluene is then distilled off and the remains are fractionated at reduced pressure. At a boiling point of 156°C/13 mm of Hg pressure, 118 g of a weakly yellow colored oil of the anil of 1-methyl-1- piperidone-4 are obtained.
100 g of the above described anil of 1-methyl-1-piperidone-4 are boiled for 8 hours, using a reflux condenser, with 30 g of activated borings of aluminum in 300 ml of methanol diluted with 60 ml of water. The liquid phase is then separated from the solid phase, the solvent is evaporated and the residuum is fractionated at reduced pressure, 95 g of a colorless oil being obtained boiling at 163-165°C at 15 mm of Hg pressure. The oil solidifies at once to a mass of crystals of 4-N-phenylaimno-1-methylpiperidine. After having been recrystallized from dibutyl ether the base melts at 87°C, its dihydrochloride has the melting point of 246°C.
95 g of 4-N-phenylamino-1-methylpiperidine are boiled together with 22 g of pulverized sodium amide in 300 ml of benzene, using a reflux condenser, while nitrogen is passed through the reaction mixture, until the evolution of ammonia has ceased. 64 g of benzyl chloride are then gradually added drop by drop to the boiling reaction product and boiling is continued for several hours. After having been cooled the solution is shaken with water and subsequently dried with potassium carbonate. The solvent having been evaporated the remaining base of 4-(N-phenyl-N-benzyl)-amino-1- methylpiperidine solidifies with the formation of crystals, the yield amounting to 123 g. The base is recrystallized from dibutyl ether and has a melting point of 115°C; its dihydrochloride melts at 189°C.

Therapeutic FunctionAntihistaminic, Antiallergic
BAMIPINE Preparation Products And Raw materials
Raw materials1-Methyl-4-piperidone-->Acetic acid-->Aniline
4-TERT-BUTYL-N-[2-METHYL-1H-INDOL-5-YL]-N-[1-(2-PHENYLETHYL)PIPERIDIN-4-YL]BENZAMIDE N-(1-ACETYL-2,3-DIHYDRO-(1H)-INDOL-6-YL)-N-(1-METHYLPIPERIDIN-4-YL)-4-(TRIFLUOROMETHYL)BENZAMIDE N-(1-ACETYLPIPERIDIN-4-YL)-N-(2-TERT-BUTYL-(1H)-INDOL-5-YL)-4-(TRIFLUOROMETHYL)BENZAMIDE N-(1-ACETYL-2,3-DIHYDRO-(1H)-INDOL-5-YL)-N-(1-PROPYLPIPERIDIN-4-YL)3-(TRIFLUOROMETHYL)BENZAMIDE N-(1-ACETYL-2,3-DIHYDRO-(1H)-INDOL-5-YL)-N-(1-ACETYLPIPERIDIN-4-YL)-4-(TRIFLUOROMETHYL)BENZAMIDE N-[1-(2,6-DIMETHOXYBENZYL)PIPERIDIN-4-YL]-N-PHENYL-3-(TRIFLUOROMETHYL)BENZAMIDE N-(1-ACETYLPIPERIDIN-4-YL)-N-[3-[(TRIFLUOROMETHYL)SULPHONYL]PHENYL]BENZAMIDE BAMIPINE N-(2-TERT-BUTYL-(1H)-INDOL-5-YL)-4-(METHYLSULPHONYL)-N-(1-PROPYLPIPERIDIN-4-YL)BENZAMIDE N-(1-BENZYLPIPERIDIN-4-YL)-N-(2-TERT-BUTYL-(1H)-INDOL-5-YL)-4-(METHYLSULPHONYL)BENZAMIDE N-(1-ACETYL-2,3-DIHYDRO-(1H)-INDOL-5-YL)-N-[1-(2-PHENYLETHYL)PIPERIDIN-4-YL]BENZAMIDE N-(1-BENZYLPIPERIDIN-4-YL)-N-(2-TERT-BUTYL-(1H)-INDOL-5-YL)-4-(TRIFLUOROMETHYL)BENZAMIDE N-(1-ACETYLPIPERIDIN-4-YL)-N-(2-TERT-BUTYL-(1H)-INDOL-5-YL)-4-(METHYLSULPHONYL)BENZAMIDE N-(1-ACETYL-2,3-DIHYDRO-(1H)-INDOL-5-YL)-N-(1-METHYLPIPERIDIN-4-YL)-4-(TRIFLUOROMETHYL)BENZAMIDE N-(2-TERT-BUTYL-(1H)-INDOL-5-YL)-2-CHLORO-N-(1-PROPYLPIPERIDIN-4-YL)BENZAMIDE N-[2,3-DIHYDRO-1-(METHYLSULPHONYL)-(1H)-INDOL-5-YL]-N-(1-METHYLPIPERIDIN-4-YL)-3-(TRIFLUOROMETHYL)BENZAMIDE N-(1-ACETYLPIPERIDIN-4-YL)-N-(2-TERT-BUTYL-(1H)-INDOL-5-YL)-3,4,5-TRIMETHOXYBENZAMIDE N-(2-TERT-BUTYL-(1H)-INDOL-5-YL)-N-(1-PROPYLPIPERIDIN-4-YL)-3-(TRIFLUOMETHYL)BENZAMIDE

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