5460-68-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(1-Aminocyclohexyl)methanol hydrochloride is used as a building block for the synthesis of various pharmaceuticals due to its ability to contribute to the formation of complex molecular structures that can exhibit therapeutic effects.
Used in Organic Chemistry:
AHMC is used as a reagent in organic chemistry for its capacity to participate in a range of chemical reactions, facilitating the creation of diverse organic compounds.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
(1-Aminocyclohexyl)methanol hydrochloride is used as a chiral auxiliary in asymmetric synthesis to assist in the production of enantiomerically pure compounds, which is crucial for the development of new drug candidates with specific biological activities.
Used in the Production of Fine Chemicals and Active Pharmaceutical Ingredients:
AHMC is utilized as a reagent in the manufacturing process of various fine chemicals and active pharmaceutical ingredients, contributing to the quality and efficacy of the final products in the pharmaceutical industry.

InChI:InChI=1/C7H15NO/c8-7(6-9)4-2-1-3-5-7/h9H,1-6,8H2

Upstream product

• 90204-86-7 N-(1-hydroxymethyl-cyclohexyl)-formamide 
• 2756-85-6 1-aminocyclohexane carboxylic acid 
• 187610-67-9 1-[1-(tert-butoxycarbonylamino)cyclohexyl]methanol 

Downstream Products

• 766550-16-7 1-benzyl-4-(1-hydroxymethylcyclohexyl)piperazine 
• 766550-27-0 1-[N-(tert-butoxycarbonyl)-4-chloro-D-phenylalanyl]-4-[1-(1,2,4-triazol-1-yl-methyl)cyclohexyl]piperazine 
• 1026858-98-9 methanesulfonic acid 1-(4-benzyl-piperazin-1-yl)-cyclohexylmethyl ester 
• 511538-97-9 1-benzyl-4-[1-(1,2,4-triazol-1-yl-methyl)cyclohexyl]piperazine 
• 511538-98-0 1-[1-(1,2,4-triazol-1-yl-methyl)cyclohexyl]piperazine 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING SUBSTITUTED AMINO ALCOHOLS

The present invention relates to a process for producing a compound of the formula (I) comprising at least the process step: a) reacting a compound of the formula (II) with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.

Ruthenium-Catalyzed Deaminative Hydrogenation of Amino Nitriles: Direct Access to 1,2-Amino Alcohols

A new approach for the efficient and highly selective synthesis of 1,2-amino alcohols by direct reductive hydrolysis of N-formyl-protected α-amino nitriles is reported. The commercially available RuHCl(CO)(PPh3)3 complex was found to be a suitable catalyst for this operationally simple protocol, in which no stoichiometric amounts of undesired metal waste are generated. The deaminative hydrogenation is performed at 55 bar of H2, using a 6:1 mixture of 1,4-dioxane/water as solvent. In addition, hydroxymethyl alcohols were prepared from cyanoketones under very similar conditions.

New substituted piperazines as ligands for melanocortin receptors. Correlation to the X-ray structure of "THIQ"

A series of piperazine analogues of the melanocortin 4 receptor (MC4R) specific small-molecule agonist "THIQ" was synthesized and characterized structurally and pharmacologically. First, several THIQ imitations lacking the triazole moiety were prepared. Syntheses included acylation of 4-phenylpiperazine or 4-cyclohexylpiperazine. In two cases the tertiary amine function was replaced by the corresponding N-oxide. To obtain more complex structures, a 4-substituted piperazine ring was formed by alkylation of the primary amino group of cyclohexane-derived amino alcohols with N,N-bis(2-chloroethyl)benzylamine. The hydroxylic group of the intermediate was first activated with methanesulfonyl chloride, and the sulfonic ester formed in situ was introduced into the reaction with the sodium salt of 1,2,4-triazole. In one case (i.e., preparation of 23c) introduction of the 1,2,4-triazole moiety was performed at a carbon of the cyclohexane ring. In addition, this intermediate contained a piperazine moiety connected via its nitrogen atom to a cyclohexane ring carbon neighboring the reaction center. As established in NMR and X-ray investigations herein, this substitution proceeded with retention of the initial trans configuration of 1,2-disubstituted cyclohexane. To obtain pure enantiomers of 23c, its precursor 21c was subjected to chiral chromatography on a Chirobiotic V column. The derivatives (R,R)-21cand (S,S)-21c obtained were introduced into further syntheses steps, giving (R,R)-23c and (S,S)-23c, respectively. Melanocortin MC1,3-5 receptor binding studies showed that all tested piperazine derivatives were active. Several compounds showed clear selectivity for MC4R, with submicromolar affinities being obtained. Among them, one substance, (R,R)-23c, displayed a biphasic curve in displacement of [125I]NDP-MSH on MC4R [K(i)high = 1 nM and K(i)low = 260 nM]. This biphasic competition curve was similarly biphasic to the competition curve obtained herein using THIQ. An X-ray study performed on crystals of the THIQ sulfate salt revealed two closely related conformations, which resemble the shape of the letter "Y", where piperidine and 4-chlorophenyl groups are situated close to each other, but the 1,2,3,4-tetrahydroisoquinoline residue is remote, the triazole function being highly exposed to the environment. The crystals of the dinitrate salt of (R,R)-23c showed a different conformation, where parts of the molecule are spread out almost symmetrically around the central section. Molecular modeling, based on the THIQ crystal structure and the functional similarity of THIQ and (R,R)-23c, allowed us to suggest a possible "bioactive" conformation of (R,R)-23c that is similar to the crystal conformation of THIQ.