N-Methyl Desloratadine Chemical Properties

Melting point:

106-109°C

Boiling point:

474.3±45.0 °C(Predicted)

Density 

1.205±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

8.67±0.20(Predicted)

form 

solid

Appearance

White to off-white Solid

Major Application

pharmaceutical small molecule

InChI

InChI=1S/C20H21ClN2/c1-23-11-8-14(9-12-23)19-18-7-6-17(21)13-16(18)5-4-15-3-2-10-22-20(15)19/h2-3,6-7,10,13H,4-5,8-9,11-12H2,1H3

InChIKey

VLXSCTINYKDTKR-UHFFFAOYSA-N

SMILES

C12/C(=C3\CCN(C)CC\3)/C3=CC=C(Cl)C=C3CCC1=CC=CN=2

CAS DataBase Reference

38092-89-6(CAS DataBase Reference)

Safety Information

WGK Germany 

WGK 3

HS Code 

2933399090

Storage Class

11 - Combustible Solids

N-Methyl Desloratadine Usage And Synthesis

Chemical Properties

Red Oil

Uses

N-Methyl Desloratadine (Loratadine EP Impurity G; Loratadine USP Related Compound B) is an intermediate in the synthesis of Loratadine. Loratadine impurity.

Uses

An intermediate in the synthesis of Loratadine. Loratadine impurity.

Synthesis

The general procedure for the synthesis of 8-chloro-11-(1-methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1 ,2-b]pyridine using (1-methyl-4-piperidinyl)[3-[2-(3-chlorophenyl)ethyl]pyridin-2-yl]methanone hydrochloride as a starting material was as follows: in Example 2, the preparation of 8-chloro-6,11-dihydro-1H -(N-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (XII). This was done by preparing Compound XIII (100 g) according to the standard method described in U.S. Patent No. 4,659,716 by first azeotropic de-watering in toluene without drying. Subsequently, boric acid (115 g) and concentrated sulfuric acid (415 g) were added and the reaction was heated at 105-110°C for 4-8 hours. After completion of the reaction, the reaction mixture was slowly poured into cold water and extracted with ethyl acetate. Finally, the solvent was removed by distillation under reduced pressure to afford the target product 8-chloro-11-(1-methylpiperidin-4-ylmethylene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine as a solid form in 85% yield and 99.5% purity (determined by OAB and HPLC).

References

[1] Journal of Organic Chemistry, 1989, vol. 54, # 9, p. 2242 - 2244
[2] Patent: WO2006/6184, 2006, A2. Location in patent: Page/Page column 17
[3] Patent: US6075025, 2000, A
[4] Patent: US5422351, 1995, A

N-Methyl Desloratadine(38092-89-6)Related Product Information

• Basic Violet 1
• Dihydromyrcenol
• Triacetonediamine
• Kresoxim-methyl
• 2,4,6-Collidine
• Azamethiphos
• 2,6-Lutidine
• Methyl acrylate
• Methylparaben
• Methanol
• Benzo[b]thien-2-ylboronic acid
• 4-Methylpyridine
• 3-[2-(3-Chlorophenyl)ethyl]-2-pyridinecarbonitrile
• 2,2,6,6-Tetramethyl-4-piperidinol
• Acetonitrile
• Methyl
• Loratadine
• 3-Hydroxy loratadine