1-bromocyclopentyl-o-chlorophenyl ketone synthesis
- Product Name:1-bromocyclopentyl-o-chlorophenyl ketone
- CAS Number:6740-86-9
- Molecular formula:C12H12BrClO
- Molecular Weight:287.58
6740-85-8
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$82.00/5g
6740-86-9
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$377.00/5g
Yield:6740-86-9 98%
Reaction Conditions:
with NBS;toluene-4-sulfonic acid in dichloromethane; for 6 h;
Steps:
Racemic norketamine hydrochloride was prepared starting from 2-chlorobenzonitrile.Treatment with cyclopentylmagnesium bromide in the presenceof copper (I) bromide, followed by hydrolysis, gave the cyclopentyl-(2-chlorophenyl) ketone (Weiberth and Hall, 1987). This was brominated with Nbromosuccinimide,followed by treatment with liquid ammonia to form animine intermediate. Thermal rearrangement of the imine afforded (R,S)-norketamine (Fig. 1). The structures of these chemicals were confirmed by1H and 13C NMR spectra with use of a Varian Gemini (300 MHz) instrument(Agilent Technologies, Mulgrave, VIC, Australia). NMR spectra were recordedin CDCl3 solution using tetramethylsilane (0 ppm) and CDCl3 (77.0 ppm) asinternal standards for 1H and 13C, respectively. Optical resolution of theenantiomers was accomplished through formation of the diastereomeric tartratesalts (Hong and Davisson, 1982).
References:
Li, Yibai;Coller, Janet K.;Hutchinson, Mark R.;Klein, Kathrin;Zanger, Ulrich M.;Stanley, Nathan J.;Abell, Andrew D.;Somogyi, Andrew A. [Drug Metabolism and Disposition,2013,vol. 41,# 6,p. 1264 - 1272]
873-32-5
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$9.00/1g
6740-86-9
61 suppliers
$377.00/5g
609-65-4
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$21.00/25g
6740-86-9
61 suppliers
$377.00/5g
142-29-0
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$14.00/25mL
6740-86-9
61 suppliers
$377.00/5g