• Name

  Zilpaterol

• EINECS
• CAS No. 117827-79-9
• Article Data4
• CAS DataBase
• Density 1.299 g/cm³
• Solubility
• Melting Point
• Formula C₁₄H₁₉N₃O₂
• Boiling Point
• Molecular Weight 261.324
• Flash Point
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms (+-)-trans-4,5,6,7-Tetrahydro-7-hydroxy-6-(isopropylamino)imidazo(4,5,1-jk)(1)benzazepin-2(1H)-one;Zilpaterol [inn];
• PSA 70.05000
• LogP 1.52420

Synthetic route

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one hydrochloride

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions

Conditions	Yield
With ammonium hydroxide In water at 20℃; for 1h;	96%
With ammonium hydroxide In water at 20℃; Product distribution / selectivity;	96%

zilpaterol-acetic acid

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 50 - 65℃; under 675.068 Torr; pH=10;

92260-82-7

4,5,6,7-tetrahydro-6-hydroxyimino-imidazo[4,5,1-jk]-[1]-benzazepine-2,7(1H,6H)-dione

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen / methanol; N,N-dimethyl-formamide / 20 - 60 °C / 750.08 - 3750.38 Torr 2: potassium carbonate / 50 °C 3: sodium tetrahydroborate; methanol / 2 h / 10 - 40 °C View Scheme

C14H17N3O2

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate at 10 - 40℃; for 2h;

501-53-1

benzyl chloroformate

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-rel-(1-methylethyl)-(4,5,6,7-tetrahydro-7-hydroxy-2-oxoimidazo[4,5,1-jk][1]benzazepin-6-yl)carbamic acid phenylmethyl ester

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetone; toluene at 10 - 20℃; for 30h; Inert atmosphere;	61%

2969-81-5

4-bromoethylbutanoate

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

4-((6S,7S)-6-Hydroxy-7-isopropylamino-1-oxo-6,7,8,9-tetrahydro-2,9a-diaza-benzo[cd]azulen-2-yl)-butyric acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

zilpaterol-butyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone / Heating 2: aq. KOH / ethanol / 1 h / Heating View Scheme

501-53-1

benzyl chloroformate

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

trans-(rac)-zilpaterol benzyl carbamate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetone; toluene at 10 - 20℃; Inert atmosphere;

117827-79-9

(6R,7R)-rel-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

A

(6R,7R)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

1001395-75-0

(6S,7S)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions

Conditions	Yield
With CHIRACEL OD-H In ethanol; hexane at 35℃; for 0.25h; Purification / work up; Resolution of racemate;

Zilpaterol Specification