76916-13-7

Basic information

• Product Name: 1,1'-(1,4-Phenylenedicyclohexylidene)bis
• CAS NO: 76916-13-7
• Molecular Weight: 408.671
• Mol File: 76916-13-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,1'-(1,4-Phenylenedicyclohexylidene)bis(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-(1,4-Phenylenedicyclohexylidene)bis(76916-13-7)
• EPA Substance Registry System: 1,1'-(1,4-Phenylenedicyclohexylidene)bis(76916-13-7)

Safety Data

• Hazardous Substances Data: 76916-13-7(Hazardous Substances Data)

Upstream product

• 3867-15-0 1-piperidinocyclohexylcarbonitrile 
• 106-37-6 1.4-dibromobenzene 
• 624-38-4 para-diiodobenzene 

Relevant articles and documents

Palladium-Catalyzed Vinylic Substitution Reactions. An Approach to (Aminoalkyl)phencyclidines

4-Iodophencyclidine (5) was reacted with various N-alkenylphthalimides in the presence of 1 mol percent palladium acetate, triethylamine, and tri-o-tolylphosphine in acetonitrile as solvent at 100 deg C to give good yields of (E)-4-(phthalimidoalkenyl)phencyclidines (9a-c).Catalytic hydrogenation of the olefins gave 12a-c, and cleavage of the phthalimido moiety gave the desired 4-(aminoalkyl)phencyclidines (2a-c) which were characterized as their mixed thioureas.Amine 2b was also synthesized by reduction of the palladium-catalyzed phencyclidine-acrylonitrile adduct.Reaction of acrolein ethylene ketal with 5 in the presence of palladium acetate did not give adduct 15 but rather gave isomerized ketene acetal 17 which underwent further reaction to 16a or hydrolyzed to 16b upon workup.Transesterification of 16 with methanol gave methyl ester 18 which was identical with the ester obtained by catalytic reduction of the palladium-catalyzed adduct of 5 and methyl acrylate, 19.LAH reduction of 19 gave a 4/1 mixture of alcohols 21 and 22.Mass spectra and 13C NMR spectra are presented for these phencyclidines.

Syntheses of Amine Derivatives of Phencyclidine

3-Aminophencyclidine (5) was synthesized by reduction of 3-nitrophencyclidine (3) using either H2 with Pd/C or Na2S in refluxing methanol.Attempts to isolate 4-aminophencyclidine (2), which we hoped to synthesize by hydrolysis of carbamate 15 which was isolated after reaction of amide 10 under Hofmann conditions employing bromine in CH3O(1-)/CH3OH at -40 deg C, were unsuccessful. 4-Aminomethylphencyclidine (18) was synthesized by LAH reduction of nitrile 13 as well as by reductive amination of aldehyde 20.Nitrile 13 and aldehyde 20 were synthesized from 4-bromophencyclidine (11) as was alcohol 26 which served as a precursor to 4-(2-aminoethyl)phencyclidine (19).Amine 19 was also synthesized by NaBH4 reduction of β-nitrostyrene 29 which was generated from aldehyde 20 by condensation with nitromethane using 1,5-diazabicycloundecene as the base catalyst followed by LAH reduction of resulting 4-(2-nitroethyl)phencyclidine (30).Mass spectra and 13C NMR spectra have been obtained on most of the phencyclidine derivatives.