79499-58-4

Basic information

• Product Name: Cyclopentanol, 1-[(2-chlorophenyl)iminomethyl]-, hydrochloride
• Synonyms: 1-((2-chlorophenyl)(imino)methyl)cyclopentanol hydrochloride
• CAS NO: 79499-58-4
• Molecular Formula: C12H14ClNO.ClH
• Molecular Weight: 260.163
• Mol File: 79499-58-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: >39°C (dec.)
• CAS DataBase Reference: Cyclopentanol, 1-[(2-chlorophenyl)iminomethyl]-, hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanol, 1-[(2-chlorophenyl)iminomethyl]-, hydrochloride(79499-58-4)
• EPA Substance Registry System: Cyclopentanol, 1-[(2-chlorophenyl)iminomethyl]-, hydrochloride(79499-58-4)

Safety Data

• Hazardous Substances Data: 79499-58-4(Hazardous Substances Data)

Usage

Uses

1-[(2-Chlorophenyl)(imino)methyl]cyclopentanol Hydrochloride is an intermediate in the synthesis of Dehydro Norketamine (D229950). Dehydro Norketamine is a metabolite of Ketamine (K165300).

Upstream product

• 6740-86-9 (1-Bromocyclopentyl)(2-chlorophenyl)methanone 
• 6740-85-8 (2-chlorophenyl)(cyclopentyl)methanone 
• 79499-57-3 (±)-1-((2-chlorophenyl)(imino)methyl)cyclopentan-1-ol 

Downstream Products

• 83777-65-5 (S)-Norketamine 
• 1430202-70-2 (2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride 
• 79499-60-8 2-Bromo-6-amino-6-(2-chlorophenyl)cyclohexanone hydrobromide 
• 35211-10-0 norketamine 

Relevant articles and documents

KETAMINE DERIVATIVES

The present invention relates to ketamine derivatives of the formula (I), pharmaceutical compositions comprising them, and methods for treating pain comprising administering them, and their use in the manufacture of medicaments for treating pain. The present invention also relates to methods for anaesthetizing and methods for sedating a subject comprising administering ketamine derivatives of the formula (II).

Synthesis of Ketamine Metabolites I and II and Some Anomalous Reactions of 6-Bromoketamine

Two metabolites of the drug ketamine, 2-(2-chlorophenyl)-2-(methylamino)cyclohexanone hydrochloride (1), have been synthesized.They are the N-demethyl compound, metabolite I (13), and the N-demethyl-5,6-dehydro analogue, metabolite II (15).Three bromo ketone derived from ketamine have also been synthesized and their realtive configuration assigned.In addition, attempted dehydrohalogenation of axial 2-bromoketamine (2a) with sodium amide in liquid ammonia has produced a novel entry into the 6-azabicycloheptane ring system.The structure of the rearrangement product (3) has been confirmed by unequivocal synthesis.Other unusual reactions include the reduction of an N-alkylazetidinone to an N-alkylazetidine and an acid-catalyzed N-alkyl cleavage of a β-lactam.