Reilly Research Report
1-Hydroxypiperidine so 2
RNCO
>Ν· OCONHR
S0 3 H
RX
RCOCI
x~ HO
OCOR
I
Ο
/ \ RHC—CH 2
ROSOX I OS02R Cu(ll),Ag(D »N"
ο.
N
o
^Nv
Ν
SIS
1-Hydroxypiperidine is a reactive hydroxylamine, undergoing the wide variety of reactions typical of dialkylhydroxylamines. Its esters exhibit selective acylating properties and can be used to prepare amides of primary aliphatic amines in the presence of primary aromatic amines. "Active esters," derived from optically active amino acids, are utilized in the synthesis of peptides possessing remarkably high optical purity. The nitrone dimer reacts with Grignard reagents to yield 2-substituted derivatives of 1-Hydroxypiperidine which, upon hydrogenolysis, are converted to the 2-substituted piperidines. The inherent reducing properties of 1-Hydroxy piperidine make it an attractive reagent for the reduction of metal ions.
RCHOH-Cri
X
0"
CH 2 =CHC0 2 Me Me0 2 CCH 2 CH 2 0
In addition to its usefulness as a versatile synthetic intermediate and as a reducing agent, 1-Hydroxy piperidine has found application in photoprocessing, polyolefin stabilization, as a polymerization inhibitor for vinyl monomers and as an anti-oxidant. Its solubility in water, aqueous acids and bases, and in organic solvents permits its incorporation into a wide variety of formulations. Specifications, data, and bibliographic information are available upon request.
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