1632-26-4

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Diazabicyclo[2.2.2]octan-3-one is used as an intermediate in the synthesis of Bicyclo Risperidone (B382800), which is an impurity of Risperidone (R525000). Risperidone is a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist, commonly used in the treatment of various psychiatric disorders such as schizophrenia, bipolar disorder, and irritability associated with autistic disorder. The synthesis of this intermediate allows for the development of more effective and safer medications for these conditions.

InChI:InChI=1/C6H10N2O/c9-6-5-1-3-8(7-6)4-2-5/h5H,1-4H2,(H,7,9)

Upstream product

• 13458-55-4 1-Nitroso-4-(carbomethoxy)piperidine 
• 97812-34-5 2-chloro-1,2-diazabicyclo(2.2.2)octan-3-one 
• 55-22-1 pyridine-4-carboxylic acid 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 

Relevant academic research and scientific papers

Nitrosohydrazine Conformations. The Effect of Replacing C(1)-H of 2-Nitroso-2-azabicyclooctane Derivatives by Nitrogen

Substitution of one and two methyl groups for hydrogens at C(3) of 2-nitroso-2-azabicyclooctane, 1, which exists entirely in the A conformation (nitroso oxygen syn to C(3)), sterically destabilizes the A conformation.The monomethyl compound (2) exists only 85percent in conformation A, and the B conformation (nitroso oxygen syn to C(1)) predominates for the dimethyl compound, 3 (13percent A, 87percent B).Replacement of C(1)-H by N gives the "homomorphic" nitrosohydrazines 4-6.The monomethyl compound 5 exists 98percent in conformation A and the dimethyl compound 6 60percent in conformation A, so the CH -> N transformation favors conformation A by 1.3 to 1.4 kcal/mol for 2 -> 5 and 3 -> 6.This result is the opposite to that predicted, considering steric, nitroso nitrogen lone pair-?*, and N(1) lone pair-nitroso nitrogen lone pair interactions.

ASYMMETRICAL NITROGEN-40; GEMINAL SYSTEM-26. N-CHLOROHYDRAZINES

The factors determining the kinetic and thermodynamic stabilities of N-chlorohydrazines are discussed.Acyclic N-chlorohydrazines exist only as trialkyldiazenium chlorides 3a,b.Chlorination of 2-acyl-1,1-dimethylhydrazines 6a,b gave 1,4-diacyl-2,3-dimethylhexahydro-1,2,4,5-tetrazines 7a,b via hydrazyl radical intermediates, and chlorination of a 1-phenylpyrazolidin-5-one 8 gave phenylazoisovaleric esters 9a,b.Stable N-chlorohydrazines were obtained from bicyclic hydrazines; viz. the 2-chloro-1.2-diazabicyclo(2.2.2.)octan-3-one 12 and 7-chloro-1,7-diazabicyclo(2.2.1)heptane 16.The restricted inversion of N(7) in 16 and its 1-methyl quate rnary salt 21 were observed in the 13C-NMR spectra.The acyclic N-chlorohydrazinium salt 25 was isolated.