2-CHLORO-N-CYCLOHEXYL-ACETAMIDE synthesis
- Product Name:2-CHLORO-N-CYCLOHEXYL-ACETAMIDE
- CAS Number:23605-23-4
- Molecular formula:C8H14ClNO
- Molecular Weight:175.66
108-91-8
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75-36-5
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23605-23-4
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Yield: 93%
Reaction Conditions:
Stage #1:cyclohexylamine;acetyl chloride in acetonitrile at 15 - 20;
Stage #2: with hydrogenchloride in water;acetonitrile
Steps:
A.1.2
Example A.I.I : General procedure 1 (GPl)The amine (2.1 equiv) was dissolved in acetonitrile (1 mL per mmol acyl halide) and added drop wise to a stirred solution of the acyl halide (1.0 equiv) in acetonitrile (1 mL per mmol acyl halide) at ca. 150C. The reaction was stirred at room temperature for 1-2 hours then the reaction was diluted with ethyl acetate (2 mL per mmol acyl halide). The organic layer was washed with aqueous hydrochloric acid (1.2 M, 1 mL per mmol acyl halide then 10 ml) and the aqueous layer was extracted with ethyl acetate (1 mL per mmol acyl halide). The combined organic layers were washed with aqueous sodium carbonate (IM, 0.5mL per mmol acyl halide), dried over magnesium sulphate, filtered and concentrated to give the product.Example A.1.2: 2-Chloro-/V-cyclohexylacetamide (002NK13)Cyclohexylamine (21 mmol, 2.08 g) and acetyl chloride (10 mmol, 1.12 g) were used according to GPl to give 2-chloro-Λ/-cyclohexylacetamide (1.631 g, 93%) as fluffy white crystals. 1H NMR (CDCI3) δ 6.44 (IH, broad s, CO-NH-CH), 4.02 (2H, s, CI-CH3), 3.89 (IH, m, CO- NH-CH), 1.92 (2H, m, cyclohexyl), 1.74 (2H, m, cyclohexyl), 1.63 (IH, m, cyclohexyl), 1.38 (2H, m, cyclohexyl), 1.25 (2H, m, cyclohexyl), 1.16 (IH, m, cyclohexyl).HPLC phosphate buffer: Rt 8.47 mins (98.5 % pure).
References:
NENSIUS RESEARCH A/S;KELLY, Nicholas;WELLEJUS, Anja;JØRGENSEN, Signe, Humle;WEIDNER, Morten, Sloth WO2011/945, 2011, A2 Location in patent:Page/Page column 36
108-91-8
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79-04-9
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23605-23-4
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593-71-5
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3173-53-3
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23605-23-4
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107-14-2
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108-93-0
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23605-23-4
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107-14-2
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110-83-8
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23605-23-4
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$45.00/25mg