histapyrrodine
histapyrrodine Basic information
- Product Name:
- histapyrrodine
- Synonyms:
-
- histapyrrodine
- 1-[2-(N-Phenylbenzylamino)ethyl]pyrrolidine
- N-benzyl-N-(2-pyrrolidin-1-ylethyl)aniline
- 1-Pyrrolidineethanamine, N-phenyl-N-(phenylmethyl)-
- Histapyrrodine USP/EP/BP
- CAS:
- 493-80-1
- MF:
- C19H24N2
- MW:
- 280.41
- EINECS:
- 207-781-9
- Mol File:
- 493-80-1.mol
histapyrrodine Chemical Properties
- Boiling point:
- bp1 198-205°
- pka
- pKa 2.99± 0.12；7.95 ± 0.02(H2O,t undefined,I=0.30(NaCl)) (Uncertain)
histapyrrodine Usage And Synthesis
Originator
Calcistin,Galenus
Definition
ChEBI: Histapyrrodine is an aromatic amine.
Manufacturing Process
3 Methods of producing of N-(β-N-phenyl-N-benzylaminoethyl)pyrrolidine:
1. A mixture of 100 parts of N-p-chloroethyl-N-benzylaniline and 100 parts of
freshly distilled pyrrolidine are heated to boiling under reflux cooling for about
10 h. Diluted aqueous caustic soda lye is added to the reaction mixture until it
shows an alkaline reaction. The reaction product formed and unchanged
pyrrolidine are extracted with ether. The extract thus obtained is a subjected
to a distillation. After the ether has evaporated, there is produced N-(β-Nphenyl-N-benzylaminoethyl)pyrrolidine, which boils at from 198° to 205°C
under 1 mm pressure.
2. 34 parts of N-β-chloroethylpyrrolidine hydrochloride are dissolved together
with 110 parts of N-benzylaniline in 400 parts of alcohol, and the solution is
heated to boiling under reflux cooling for 15 h, while adding 0.5 part of
copper powder. After filtering off the copper powder and driving off the
alcohol, dilute caustic soda solution is added until the solution shows an
alkaline reaction, whereupon the oil separated is distilled in vacuum. After a
forerun of excess N-benzylaniline, there passes over as a main fraction the N-
(β-N-phenyl-N-benzylaminoethyl)pyrrolidine, which boils at between 198° and
205°C under 1 mm pressure (mercury gauge).
3. 34 parts of N-β-chloroethylpyrrolidine hydrochloride are added to a solution
of 120 parts of aniline in 500 parts of alcohol and the mixture is heated to
boiling under reflux cooling for 12 h. After rendering the mixture alkaline by
adding caustic soda solution, the excess aniline is driven off with steam. The
N-(β-N-phenylaminoethyl)pyrrolidine left is fractionated in vacuo (boiling point
160° to 165°C), 98 parts of this compound are dissolved in 250 parts of 10%
aqueous caustic soda solution and admixed with 65 parts of bensylchloride
while vigorously stirring at from 50° to 60°C. The temperature is raised to 80°
to 90°C for 1 h and the product worked up as indicated in the preceding
examples. There is obtained the N-(β-N-phenyl-N-benzylaminoethyl)
pyrrolidine in a 95% yield.
In practice it is usually used as hydrochloride.
Therapeutic Function
Antihistaminic