Water → [5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-isoxazol-3-yl]-(4-methyl-piperazin-1-yl)-methanone

HRID 389935Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([Cl:30])=[CH:18][C:17]=1[C:31]1[O:35][N:34]=[C:33]([C:36]([O:38]CC)=O)[CH:32]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.CCOC(C)=O>CCO>[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([Cl:30])=[CH:18][C:17]=1[C:31]1[O:35][N:34]=[C:33]([C:36]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:38])[CH:32]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

N-methylpiperazine (25.4 mmol) was added to a suspension of ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate (2.1 mmol) in EtOH (5 ml) and the reaction mixture was heated to 90° C. under stirring for 18 h. The reaction mixture was poured into a mixture of water (15 ml) and AcOEt (30 ml). After standard extraction, the organic layer was washed with water and brine, dried over Na2SO4, and evaporated. The resulting solid was purified by silica gel column chromatography (CHCl3/MeOH: 95/0.5) to give the desired compound (620 mg, 57%).

Workup

extractionAfter standard extraction
washthe organic layer was washed with water and brine
dry with materialdried over Na2SO4
customevaporated
customThe resulting solid was purified by silica gel column chromatography (CHCl3/MeOH: 95/0.5)

Sources & evidence

ORD record: ord-d02aaf6922c042feafff84b874da17c9
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383616B2

Reaction notes

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