Synthesis Of 4-Methoxyphenyl Cycloalkanol

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1-[Cyano(4-methoxyphenyl)methyl]cycloalkanol (VF-I) synthesized through the reaction of p-methoxyphenylacetonitrile and cyclohexanone using aq. NaOH and tetrabutylammonium hydrogen sulfate as PTC.

NaBH4 and CoCl2 in 2:1 THF: H2O used for the reduction of VF-I to obtain 1-(2-amino-1-(4-methoxyphenyl)ethyl)cyclohexanol (VF-II).

Further, venlafaxine derivative of the amino acid -carboxamide (VFCA-I toVII ) synthesized through coupling of N-Phthaloyl amino acid chloride derivative (2a-2g- synthesis reported in chapter-1) with 1-(2-amino-1-(4-methoxyphenyl) ethyl)cyclohexanol (VF-II).

All the chemicals used are of laboratory grade and purchased from local commercial suppliers and used without further purification. Melting points determined
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The progress of the reaction monitored on TLC .After 1 h TLC show traces of starting material, so additional NaBH4 (0.01 mmol) added. After 2 hours , 25 % NH4OH solution (2 ml) added and stir for 10-15 min. The Solid filtered off and washed with solvent mixture. The combined filtrate concentrated at reduced pressure to remove THF , then the aqueous residue extracted with 2 X 40 ml ethyl acetate. The combined ethyl acetate layers washed with water and dried over MgSO4. To this ethyl acetate layer, 2ml of glacial acetic acid added and stirred the reaction mixture at room temperature to afford acetate salt of 1-(2-amino-1-(4-methoxyphenyl)ethyl) cyclohexanol …show more content…
Venlafaxine is antidepressant drug. As a part of work, we have herein reported the derivative of venlafaxine having free NH2 group. Synthesis of venlafaxine derivative of the amino acid–carboxamidehave been carried out via Coupling of N-phthaloyl derivatives of the amino acid (1a-1g/2a-2g) are reported as a significant antibacterial drug. Venlafaxine is an antidepressant drug. The free amino analogue of venlafaxine (VF-II) also shows potential activity against some bacteria/ fungi. The synthesis of VF-II carried out by the novel method using a unique combination of NaBH4 /CoCl2 as a reducing agent for reduction of nitrile group. We have herein reported the coupling product of the free amino derivative of venlafaxine (VF-II) with N-phthaloyl derivatives of the amino acid (1a-1g/2a-2g) i.e. carboxamide (-CONH) VFCA –I to VII. Compounds VFCA –I to VII screened for their antibacterial study and they shows potent antibacterial activity. Molecular docking study of VFCA –I to VII carried out. All the compounds found to possess excellent binding affinity with Bovine Serum Albumin (BSA) protein. We believed that it will discover new horizons of series of potent bioactive

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