AL-1095, is a centrally acting

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

drug with comparable effects to

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

, developed by Bristol in the 1970s.

Synthesis

The first-step is a mixed-aldol condensation between 3-quinuclidinone 731-38-2(1) and

benzaldehyde Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful. It is a colorless liquid with a characteristic almond-li ...

(2) gives 2-benzylidene-3-oxoquinuclidine 4123-89-5(3). The conjugate addition of the Grignard reagent formed from 4-

bromochlorobenzene Bromochlorobenzenes are mixed aryl halides (aryl chloride and aryl bromide) consisting bromine and chlorine as substituents on a benzene ring. All three have been synthesized by various routes: * 1-Bromo-2-chlorobenzene: from 2-chloroaniline, vi ...

06-39-8(4) to the enone gives the benzhydryl (5).

MPV reduction MPV or mpv may refer to: Vehicles Road * Multi-purpose vehicle, a car class ("minivan" in North America) ** Compact MPV, a medium-sized MPV ** Mini MPV, a small MPV *Mazda MPV or Ɛ̃fini MPV, a minivan model Maritime * Multi-purpose vessel, a shi ...

of the carbonyl gives the syn stereoisomers, whereas borohydride gave trans. Both diastereoisomers are active but in only one of the enantiomers.

References

Stimulants 2-Benzylpiperidines Quinuclidines 4-Chlorophenyl compounds Secondary alcohols {{nervous-system-drug-stub

Synthesis

See also

References