73404-00-9

Usage

Uses

Used in Cardiovascular Applications:
Phenoxybenzamine is utilized as a therapeutic agent for the management of high blood pressure. Its alpha-blocking properties help in reducing the force of heart contractions and relaxing the blood vessels, thereby lowering blood pressure.
Used in Heart Disease Treatment:
In the context of certain types of heart disease, phenoxybenzamine is employed as a treatment to alleviate symptoms and improve cardiac function. Its ability to dilate blood vessels can enhance blood flow and reduce the workload on the heart.
Used in Endocrine Tumor Management:
Phenoxybenzamine is also used in the treatment of specific endocrine tumors, where its alpha-blocking action can help control symptoms associated with excessive hormone production.
Used in Off-Label Treatments:
Although not officially approved for these uses, phenoxybenzamine is applied off-label for conditions such as Raynaud's syndrome and complex regional pain syndrome. Its vasodilatory effects can provide relief from symptoms caused by abnormal blood flow.
Used in Pharmaceutical Formulations:
Phenoxybenzamine is typically administered orally or intravenously under medical supervision. This method of administration ensures that the medication reaches the bloodstream effectively and provides the desired therapeutic effects.

InChI:InChI=1/C26H31NO2/c1-3-27(4-2)19-20-29-25-17-15-24(16-18-25)26(28,23-13-9-6-10-14-23)21-22-11-7-5-8-12-22/h5-18,28H,3-4,19-21H2,1-2H3

Synthetic route

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → 2-{4-[(Z)-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanaminium hydrogen sulfate

Conditions	Yield
With sulfuric acid In dichloromethane at 0 - 20℃; for 1h;	100%

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → clomiphene citrate (7599-79-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid / dichloromethane / 1 h / 0 - 20 °C 2.1: N-chloro-succinimide / dichloromethane / 32 h / 20 °C 2.2: 0.5 h / 20 °C / pH 8 - 9 3.1: methanol / 2 h / 20 °C 4.1: ammonia / ethyl acetate 4.2: 1 h / 20 °C View Scheme

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → clomiphene (911-45-5, 15690-55-8, 15690-57-0) + Zuclomiphene (911-45-5, 15690-55-8, 15690-57-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol / 3 h / 50 °C / Reflux 2.1: N-chloro-succinimide / dichloromethane / 20 h / 20 °C 2.2: 0.5 h / 20 °C View Scheme

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → 2-{4-[(Z)-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanaminium hydrochloride

Conditions	Yield
With hydrogenchloride In ethanol at 50℃; for 3h; Reflux;

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → clomiphene (911-45-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / dichloromethane / 1 h / 0 - 20 °C 2.1: N-chloro-succinimide / dichloromethane / 32 h / 20 °C 2.2: 0.5 h / 20 °C / pH 8 - 9 View Scheme

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → ethanamine, 2-[4-[(1E)-2-chloro-1,2-diphenyl ethenyl]phenoxy]-N,N-diethyl-, (±)-1,1‘-binaphthyl-2,2’-diylhydrogenphosphate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / dichloromethane / 1 h / 0 - 20 °C 2.1: N-chloro-succinimide / dichloromethane / 32 h / 20 °C 2.2: 0.5 h / 20 °C / pH 8 - 9 3.1: methanol / 2 h / 20 °C View Scheme

Downstream Products

• 911-45-5 clomiphene 
• 74056-26-1 2-{4-[(Z)-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanaminium hydrochloride 
• 911-45-5 clomiphene 
• 911-45-5 Zuclomiphene 
• 7599-79-3 clomiphene citrate