Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride
نویسندگان
چکیده
1-Cyclopropylcyclopropanecarboxylic acid (2), which is accessible on a large scale (900 mmol) from 1-bromo-1-cyclopropylcyclopropane (1) in 64% yield (89% on a 12.4 mmol scale), has been subjected to a Curtius degradation employing the Weinstock protocol to furnish the N-Boc-protected (1-cyclopropyl)cyclopropylamine 3 (76%). Deprotection of 3 with hydrogen chloride in diethyl ether gave the (1-cyclopropyl)cyclopropylamine hydrochloride (4·HCl) in 87% yield.
منابع مشابه
Effect of 2-(p-chlorophenyl)cyclopropylamine on 5-hydroxyindole concentration and monoamine oxidase activity in rat brain.
p-Chloroamphetamine (PCA) causes a rapid and long-lasting depletion of serotonin in rat brain [l]. PCA is thought to affect serotonin neurons acutely by (a) inhibition of tryptophan hydroxylation, (b) release of vesicular bound serotonin, (c) inhibition of serotonin reuptake from the synaptic cleft, and (d) inhibition of serotonin oxidation by monoamine oxidase, and to produce neurotoxic degene...
متن کاملIsomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analogue.
The hallucinogen analogue trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine was modified by adding a 3-methyl group, either cis or trans with respect to the amino group. These two isomeric cyclopropyl ring-methylated compounds were then tested for activity in the mouse ear-scratch assay and for a contractile effect in the rat fundus preparation. Neither compound was found to possess apprec...
متن کاملAn efficient and safe process for the preparation of ticagrelor, a platelet aggregation inhibitor via resin-NO2 catalyzed formation of triazole ring
An efficient, safe and improved process for the preparation of ticagrelor 1, a platelet aggregation inhibitor is described. Synthesis comprises the condensation of pyrimidine amine derivative 14 with cyclopentyl derivative 13 in ethylene glycol followed by construction of triazole compound 16 by diazotization of the obtained intermediate 15 with a green and safer reagent "Resin-NO2" in water an...
متن کاملLong-range electron and hole transport through DNA with tethered cyclometalated iridium(III) complexes.
A cyclometalated complex of Ir(III) is covalently tethered to DNA oligonucleotides and serves as both a photooxidant and photoreductant in the study of DNA-mediated hole transport (HT) and electron transport (ET). Spectroscopic and melting temperature studies support intercalation of the tethered complex into the DNA duplex through the functionalized dppz ligand. Using these tethered assemblies...
متن کاملSimple and Sensitive Stability-Indicating Ion Chromatography Method for the Determination of Cyclopropylamine in Nevirapine and Moxifloxacin Hydrochloride Drug Substances
A simple and sensitive ion chromatography method has been developed for the determination of cyclopropylamine (CPA) in nevirapine (NEV) and moxifloxacin HCl (MOX) pharmaceutical drug substances. Efficient chromatographic separation was achieved on a Metrosep C4, 5 μm (250 mm × 4.0 mm) column. The mobile phase consists of 5 mM hydrochloric acid containing 10% (v/v) acetonitrile and was delivered...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 7 شماره
صفحات -
تاریخ انتشار 2011