Dimethyl Sulfoxide → HCID 70539474, compound
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][CH2:12][CH2:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:10])=[CH:4][CH:3]=1.CS(C)=[O:29].[OH-:31].[Na+].[C:33]([C:37]1[CH:44]=[CH:43][C:40]([CH2:41]Cl)=[CH:39][CH:38]=1)([CH3:36])([CH3:35])[CH3:34].[OH2:45]>>[C:2]([OH:1])(=[O:29])/[CH:7]=[CH:6]\[C:5]([OH:45])=[O:31].[C:33]([C:37]1[CH:38]=[CH:39][C:40]([CH2:41][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([NH:11][CH2:12][CH2:13][CH:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH3:10])=[CH:6][CH:7]=2)=[CH:43][CH:44]=1)([CH3:36])([CH3:34])[CH3:35]Participants
6
Procedure
The mixture of 18.3 g of 1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 100 ml of dimethylsulfoxide and 5.29 ml of 10 N-aqueous sodium hydroxide is stirred at room temperature for one hour, combined with 9.66 g of 4-t-butylbenzyl chloride and stirred 18 hours longer. It is poured into 1,000 ml of water, extracted twice with 500 ml of methylene chloride, the extract dried and evaporated at about 60°. The residue is taken up in isopropanol, the solution acidified with 5% isopropanolic maleic acid, the precipitate collected and recrystallized from isopropanol-diethyl ether, to yield the 1-[4-(4-t-butylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane maleate melting at 132°-134°.
Workup
- stirringstirred 18 hours longer
- extractionextracted twice with 500 ml of methylene chloride
- customthe extract dried
- customevaporated at about 60°
- customthe precipitate collected
- customrecrystallized from isopropanol-diethyl ether
Sources & evidence
- ORD record
- ord-846945c261a44b5bb2d515c2831917e0
- Source dataset
- uspto-grants-1982_05
- Patent number
- US04329367
Reaction notes
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