RAC-4-(3'-METHOXY-A-CHLOROBENZYL)-N,N-DIETHYLBENZAMIDE synthesis
- Product Name:RAC-4-(3'-METHOXY-A-CHLOROBENZYL)-N,N-DIETHYLBENZAMIDE
- CAS Number:186094-10-0
- Molecular formula:C19H22ClNO2
- Molecular Weight:331.84
186094-06-4
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186094-10-0
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Yield:186094-10-0 95%
Reaction Conditions:
with hydrogenchloride in chloroform;water at 20; for 14 h;
Steps:
3.1.e
e. Preparation of 4-[chloro-(3'-methoxyphenyl)methyl]-N,N-diethylbenzamide 5.08 grams of N,N-diethyl-4-[hydroxy-(3'-methoxyphenyl)methyl]benzamide (3.1d) are dissolved in 18 ml of chloroform. To this solution 37% by weight HCl (135 equivalents) is added. The reaction mixture is stirred at room temperature for 14 hours, then diluted with water and extracted with chloroform (50 ml for three times). The pooled organic phases are dehydrated with sodium sulphate, filtered and evaporated. 4-[chloro-(3'-methoxyphenyl)methyl]-N,N-diethylbenzamide is obtained. Yield: 95%. IR (nujol) (λ=cm-1) 1680 (C=O); 1H-NMR (CDCl3) δ 1.00-1.78 (m, 6H); 3.08-3.38 (m, 2H); 3.40-3.60 (m, 2H); 3.80 (s, 3H); 6.09 (s, 1H); 6.80-7.00 (m, 4H); 7.35 (d, 2H, J=8.4 Hz); 7.44 (d, 2H, J=8.4 Hz). Anal. calc. for C19H22ClNO2: C, 68.77; H, 6.68; N, 4.22. Found: C, 68.59; H, 6.67; N, 4.21.
References:
NEUROSCIENZE PHARMANESS S.C. A.R.L. US2011/152238, 2011, A1 Location in patent:Page/Page column 49
156727-76-3
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186094-10-0
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156727-77-4
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186094-10-0
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82520-37-4
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186094-10-0
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58287-77-7
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186094-10-0
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