Dimethylformamide → Ethyl 4-[2-[4-(4-tert-butoxycarbonyl-1-piperazinyl)phenoxy]-4-chlorophenyl]aminobutyrate

HRID 1373262Notes

Reaction equation

[NH2:1][C:2]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.Br[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][C:3]3[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:2]=3[NH:1][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:6][CH:7]=2)[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tert-butyl 4-[4-(2-amino-5-chlorophenoxy)phenyl]piperazine-1-carboxylate (3.8 g, 9.5 mmols), ethyl 4-bromobutyrate (2.7 ml, 19 mmols), potassium carbonate (1.3 g, 9.5 mmols) and N,N-dimethylformamide (30 ml) was stirred at 60° C. for 72 hours. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give an oil of ethyl 4-[2-[4-(4-tert-butoxycarbonyl-1-piperazinyl)phenoxy]-4-chlorophenyl]aminobutyrate (3.5 g, 71%).

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried with anhydrous magnesium sulfate
concentrationThis was concentrated under reduced pressure
customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record: ord-5b3e547447a546caa81f58dd9706a51f
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160887B1

Reaction notes

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