Dimethyl Sulfoxide → 5-[4-(4-Phenyl-1-piperazinyl)butyryl]-2-benzyloxy-salicylamide

HRID 65210Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]([CH:15]=1)[C:12]([NH2:14])=[O:13])=[O:6].[C:24]1([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.CS(C)=[O:45]>O>[C:24]1([N:30]2[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][CH2:4][C:5]([C:7]3[CH:8]=[CH:9][C:10]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)([OH:45])[CH:11]([CH:15]=3)[C:12]([NH2:14])=[O:13])=[O:6])[CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1 g of 5-(4-chlorobutyryl)-2-benzyloxy-benzamide, 1.2 g of 1-phenylpiperazine, 3.3 ml of triethylamine and 10 ml of dimethyl sulfoxide was heated at 90° C. for 15 hours while stirring. After the reaction was finished, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water saturated with sodium chloride, dried over anhydrous sodium sulfate and concentrated. The thus-produced residue was crystallized from ethyl acetate-ether to obtain 1.6 g of 5-[4-(4-phenyl-1-piperazinyl)butyryl]-2-benzyloxy-salicylamide (yield: 58.0%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water saturated with sodium chloride
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe thus-produced residue was crystallized from ethyl acetate-ether

Sources & evidence

ORD record: ord-8651dec700a0474fb4974b77b5371a3b
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04613598

Reaction notes

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