4-(2-Piperidinoethoxy)benzoic acid hydrochloride → 6-Benzoyloxy-2-(4-benzoyloxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Participants

Reaction Steps

The process of this example was run as was the process of Example 9, starting with the acid chloride formed from 18.9 g. of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, and 20 g. of 6-benzoyloxy-2-(4-benzoyloxyphenyl)benzo[b]thiophene. The reaction mixture was stirred for 1.5 hours, and was then worked up as described in Example 9 to obtain the desired product as an oil. A small portion of the crude product was crystallized from denatured ethanol to provide an analytical sample, m.p. 230°-233°, the identity of which was confirmed by nmr analysis. δ1.30-2.50 (6H, m, NH(CH2CH2)2CH2); 2.50-3.75 (6H, m, NH(CH2CH2)2CH2 and OCH2CH2N); 4.56 (2H, m, OCH2CH2N); 6.77 (2H, d, J=9 Hz, aromatic o to OCH2); 7.10 (2H, d, J=9 Hz, aromatic o to OCO); 7.10-7.90 (17H, m, aromatic); 8.00-8.27 (6H, m, aromatic o to CO); 12.30-12.80 (1H, broad s, NH).

Provenance & Evidence