129-74-8

Basic information

• Product Name: BUCLIZINE, DIHYDROCHLORIDE
• Synonyms: piperazine,1-[(4-chlorophenyl)phenylmethyl]-4-[[4-(1,1-dimethylethyl)phenyl]me;softran;BUCLIZINE 2HCL;Histabutizine dihydrochloride;UCB-4445, Buclina, Longifene, Posdel, Vibazine;1-[(4-Chlorophenyl)phenylmethyl]-4-[[4-(tert-butyl)phenyl]methyl]piperazine dihydrochloride;1-(4-(tert-Butyl)benzyl)-4-((4-chlorophenyl)(phenyl)Methyl)piperazine dihydrochloride;Buclizine Hydrochloride(BP/EP)
• CAS NO: 129-74-8
• Molecular Formula: C28H35Cl3N2
• Molecular Weight: 505.95
• EINECS: 204-962-4
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 129-74-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 230-240°C
• Boiling Point: 520.1 °C at 760 mmHg
• Flash Point: 268.3 °C
• Appearance: /
• Vapor Pressure: 6.44E-11mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: BUCLIZINE, DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BUCLIZINE, DIHYDROCHLORIDE(129-74-8)
• EPA Substance Registry System: BUCLIZINE, DIHYDROCHLORIDE(129-74-8)

Safety Data

• Hazardous Substances Data: 129-74-8(Hazardous Substances Data)

Usage

Chemical Properties

BUCLIZINE, DIHYDROCHLORIDE is Off-White Powder

Originator

Longifine,UCB

Uses

BUCLIZINE, DIHYDROCHLORIDE used as an antiemetic

Manufacturing Process

1 mol 4-chlorobenzhydril chloride was heated in toluene to reflux with 1 mol ethyl ester of piperazine 1-carboxylic acid at about 150°C in a presence of an excess of triethyl amine. On cooling the triethyl amine hydrochloride was filtered off, a solvent was removed in vacuum and the residue [(4-chlorophenyl)- phenyl-methyl]piperazine carboxylic acid ethyl ester was boiled straight away with potassium hydroxide in ethanol for 48 hours. After removing ethanol in vacuum to dryness, the residue was dissolved in benzene and washed with water. The benzene solution was dried, benzene removed in vacuum. The residue was distilled to give 4-chlorobezhydryl-piperazine. It had given the desired 1-(p-tert-butylbenzyl)-4-(p-chloro-α-phenylbenzyl)- piperazine, buclizine, by a reaction with 4-tert-butylbenzyl chloride in the presence of any halogen hydrochloride acceptor (triethyl amine, sodium or potassium carbonate and so on). The obtained product had BP: 230°- 240°C/0.001 mm Hg.

Brand name

Bucladin (Stuart).

Therapeutic Function

Antihistaminic, Antiallergic, Antinauseant, Tranquilizer, Appetite stimulant

General Description

Buclizine hydrochloride, l-(p-tertbutylbenzyl)-4-(p-chloro-α-phenylbenzyl)piperazinedihydrochloride (Bucladin-S), is a white to slightly yellowcrystalline powder that is insoluble in water. The highlylipid-soluble buclizine has CNS depressant, antiemetic, andantihistaminic properties. This drug has been discontinued inthe United States.

Safety Profile

Poison by intraperitoneal route. An experimental teratogen. When heated to decomposition it emits very toxic fumes of NOx, and HCl.

InChI:InChI=1/C28H33ClN2.2ClH/c1-28(2,3)25-13-9-22(10-14-25)21-30-17-19-31(20-18-30)27(23-7-5-4-6-8-23)24-11-15-26(29)16-12-24;;/h4-16,27H,17-21H2,1-3H3;2*1H

Synthetic route

buclizine dihydrochloride (129-74-8) → Buclifen (82-95-1)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃; pH=5.8;

buclizine dihydrochloride (129-74-8) → buclizine monohydrochloride

Conditions	Yield
In ethanol; water at 75℃;

Downstream Products

• 82-95-1 Buclifen