972-02-1

Basic information

• Product Name: Difenidol
• Synonyms: 1,1-Diphenyl-4-(1-piperidinyl)-1-butanol;1-Piperidinebutanol, alpha,alpha-diphenyl-;alpha,alpha-Diphenyl-1-piperidinebutanol;Benzhydrol, alpha-(3-piperidinopropyl)-;Nometic;SK&F No. 478-A;SK&F-478;SKF 478
• CAS NO: 972-02-1
• Molecular Formula: C₂₁H₂₇NO
• Molecular Weight: 309.45
• EINECS: 213-540-9
• Mol File: 972-02-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 104-105°
• Boiling Point: 449.71°C (rough estimate)
• Flash Point: 233.5 °C
• Appearance: /
• Density: 1.0350 (rough estimate)
• Refractive Index: 1.5614 (estimate)
• CAS DataBase Reference: Difenidol(CAS DataBase Reference)
• NIST Chemistry Reference: Difenidol(972-02-1)
• EPA Substance Registry System: Difenidol(972-02-1)

Safety Data

• Hazardous Substances Data: 972-02-1(Hazardous Substances Data)

Usage

Originator

Vontrol,SKF,US,1967

Definition

ChEBI: A tertiary alcohol that is butan-1-ol substituted by two phenyl groups at position 1 and a piperidin-1-yl group at position 4.

Manufacturing Process

2.6 grams magnesium, activated by means of iodine, is introduced into 20 cc of absolute ether and is caused to react with 0.6 cc of ethyl omide. While warming gently, 16.2 grams (0.1 mol) of N-[1-chloropropyl-(3)]-piperidine in 40 cc of absolute ether are added and, after adding a further 0.5 cc of ethyl omide, 14.5 grams (0.08 mol) of benzophenone in 50 cc of anhydrous ether are added in portions. The magnesium is used up fairly quickly and, after 10 hours, only traces are left. In working up, both with hydrochloric acid and with ammonium chloride, the hydrochloride of diphenyl-3-piperidinopropyl carbinol is precipitated as a dense precipitate. It is purified by recrystallization from chloroform-ethyl acetate. MP 212-214°C.

InChI:InChI=1/C21H27NO/c23-21(19-11-4-1-5-12-19,20-13-6-2-7-14-20)15-10-18-22-16-8-3-9-17-22/h1-2,4-7,11-14,23H,3,8-10,15-18H2

Upstream product

• 110-89-4 piperidine 
• 63645-18-1 4-hydroxy-4,4-diphenylbutyl chloride 
• 119-61-9 benzophenone 
• 201230-82-2 carbon monoxide 
• 3923-51-1 1,1-diphenylprop-2-en-1-ol 

Downstream Products

• 29869-89-4 1-(4,4-diphenylbut-3-enyl)piperidine 

Relevant articles and documents

Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: A new access to 4,4-diarylbutylamines

Pharmacologically active 4,4-diarylbutylamines like Fluspirilene and 4-amino-1,1-diarylbutan-1-ols like Difenidol were prepared in high yields via rhodium catalysed hydroaminomethylation of 1,1-diaryl-allylalcohols. Conversion of these olefins with carbon monoxide, hydrogen and secondary amines proceeds with complete regioselectivity. This group can easily be removed under acidic and hydrogenating conditions, enabling the transformation of 4-amino-1,1-diarylbutan-1-ols to 4,4-diarylbutylamines in high yields. Thus Fluspirilene was synthesised in 88% yield in four steps starting from commercially available materials. Graphical Abstract.