ChemicalBook CAS DataBase List RAC-4-(3'-METHOXY-A-CHLOROBENZYL)-N,N-DIETHYLBENZAMIDE

RAC-4-(3'-METHOXY-A-CHLOROBENZYL)-N,N-DIETHYLBENZAMIDE synthesis

9synthesis methods

Product Name:RAC-4-(3'-METHOXY-A-CHLOROBENZYL)-N,N-DIETHYLBENZAMIDE
CAS Number:186094-10-0
Molecular formula:C19H22ClNO2
Molecular Weight:331.84

rac-4-(3’-Methoxy-α-hydroxybenzyl)-N,N-diethylbenzamide

186094-06-4
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RAC-4-(3'-METHOXY-A-CHLOROBENZYL)-N,N-DIETHYLBENZAMIDE

186094-10-0
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$110.00/50mg

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

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156727-76-3 Synthesis