42036-65-7

Usage

Chemical Properties

white crystalline powder

Uses

An impurity found in Tramadol (T712500).

InChI:InChI=1/C9H17NO/c1-10(2)7-8-5-3-4-6-9(8)11/h8H,3-7H2,1-2H3/p+1/t8-/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 506-59-2 N,N-dimethylammonium chloride 
• 108-94-1 cyclohexanone 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 

Downstream Products

• 825-63-8 trans-2-dimethylaminomethyl-cyclohexylamine 
• 10545-22-9 1-Chlor-2-dimethylaminomethyl-cyclohexen-⁽¹⁾ 
• 53369-72-5 2-dimethylaminomethyl-cyclohexanone oxime 
• 116673-75-7 2-[(benzyl-methyl-amino)-methyl]-cyclohexanone 
• 86488-93-9 2-<(diphenylphosphinyl)methyl>cyclohexanone 
• 2478-21-9 2,6-bis(dimethylaminomethyl)cyclohexan-1-one 
• 6333-28-4 2-dimethylaminomethyl-6-piperidinomethyl-cyclohexanone; dihydrochloride 
• 117241-41-5 (+/-)-cis-1-(Dimethylamino-methyl)-cyclohexanol-⁽²⁾ 
• 117241-42-6 (+/-)-trans-2-Dimethylaminomethyl-cyclohexanol 
• 950-28-7 3,4,5,6,7,8-hexahydrospiro(chromen-2,1'-cyclohexane)-2'-one 

Relevant academic research and scientific papers

Continuous-Flow Synthesis of Tramadol from Cyclohexanone

A multioperation, continuous-flow platform for the synthesis of tramadol, ranging from gram to decagram quantities, is described. The platform is segmented into two halves allowing for a single operator to modulate between preparation of the intermediate by Mannich addition or complete the fully concatenated synthesis. All purification operations are incorporated in-line for the Mannich reaction. 'Flash' reactivity between meta-methoxyphenyl magnesium bromide and the Mannich product was controlled with a static helical mixer and tested with a combination of flow and batch-based and factorial evaluations. These efforts culminated in a rapid production rate of tramadol (13.7 g°h -1) sustained over 56 reactor volumes. A comparison of process metrics including E-Factor, production rate, and space-time yield are used to contextualize the developed platform with respect to established engineering and synthetic methods for making tramadol.

Opioid Detection

An immunoassay method is described which detects O-desmethyltramadol only. This enables an assay of high sensitivity and specificity avoiding false positive results. The unique antibodies incorporated in the immunoassay method can be combined with antibodies which detect mitragynine to provide an assay which increases the possibility of detecting the commonly found drug combination of O-desmethyltramadol and mitragynine.

Microwave-assisted regioselective synthesis of β-aminoketones via the Mannich reaction

A new and efficient method for the regioselective synthesis of β- aminoketones has been achieved by a simple reaction of formaldehyde, a secondary amine and a ketone under microwave irradiation.

Efficient Preparation of Substituted 5,6,7,8-Tetrahydroquinolines and Octahydroacridine Derivatives

The reaction of the enamine 4 with different β-amino ketone hydrochlorides 3a-e affords the diketones 5a-e which can be cyclized to the corresponding mono- and disubstituted tetrahydroquinolines 6a-e. Furthermore the preparation of the octahydroacridines 8f and 8g by using a straightforward multi step sequence is described.

Evaluation of some Mannich bases of cycloalkanones and related compounds for cytotoxic activity

A number of Mannich bases of cycloalkanones and related quaternary ammonium compounds were prepared for cytotoxic evaluation in order to examine the theory that sequential release of alkylating agents produces increased bioactivity compared to related compounds containing only 1 potential alkylating site.Many of the compounds had significant activity against murine L1210 cells and various human tumours.Some correlations between structure and activity were noted but the biological data did not support the view that potential sequential liberation of cytotoxic species produced compounds with increased potency.The formation of various oximes and oxime benzoates as candidate prodrugs was achieved but in general these compounds were not cytotoxic at the concentrations utilized.This observation may be due to the fact that the oximes were much more stable in deuterated phosphate buffered saline over a period of 48 h at 37 deg than the Mannich bases, as revealed by 1H-NMR spectroscopy. Mannich bases / cytotoxic evaluations / prodrugs / 1H-NMR spectroscopy / structure-activity relationships

EPSP SYNTHASE: THE DESIGN AND SYNTHESIS OF BISUBSTRATE INHIBITORS INCORPORATING NOVEL 3-PHOSPHATE MIMICS

Novel aromatic bisubstrate inhibitors of the enzyme EPSP (5-enolpyruvoylshikimate-3-phosphate) synthase (EC 2.5.1.19) have been designed and synthesized as structural analogs of the single, catalytic intermediate 1 utilized by the enzyme.These aromatic inhibitors incorporate novel α-hydroxyphosphonates, malonate ethers and α-hydroxymalonates as replacements for the hydrolytically labile 3-phosphate group.These 3-phosphate mimics were much preferred to the corresponding methylene and vinylic phosphonates, malonates and phosphonomethyl ethers.

β-Amino Ketones as Key Intermediates in the Synthesis of Pyridines: A Novel and Efficient Route to Annelated Bi- and Terpyridines

The hydrochlorides of β-amino ketones 1a-e (Mannich bases) are easily obtained starting compounds for a novel synthesis of pyridines.Condensation with the heteroaromatic ketones 8, 9, and 10 yields 5,6-dihydro-1,10-phenanthrolines 3a-d, 13 and 4,5-diazafluorenes 4a-d, which have not yet been described in literature.Symmetrical terpyridines 3e, 4e are formed in a one-step reaction of 8, 9 with dimethylmethylenammonium chloride in the presence of an ammonia source.