4-(2-Piperidinoethoxy)benzoic acid hydrochloride → 6-Benzoyloxy-2-(4-benzoyloxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride
Reaction equation
[ClH:1].[N:2]1([CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:20]([O:28][C:29]1[CH:30]=[CH:31][C:32]2[CH:36]=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([O:43][C:44](=[O:51])[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[CH:39][CH:38]=3)[S:34][C:33]=2[CH:52]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[ClH:1].[C:20]([O:28][C:29]1[CH:30]=[CH:31][C:32]2[C:36]([C:15](=[O:17])[C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][N:2]4[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]4)=[CH:19][CH:18]=3)=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([O:43][C:44](=[O:51])[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)=[CH:39][CH:38]=3)[S:34][C:33]=2[CH:52]=1)(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1Participants
Procedure
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).
Workup
- customformed from 18.9 g
Sources & evidence
- ORD record
- ord-1fd0ca54f67446c18398d019e54e8d09
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04358593
Reaction notes
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