Water → 4-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)butyl acetate

HRID 655639Notes

Reaction equation

Cl.[S:2]1[CH:6]=[CH:5][C:4]2[C:7]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=[CH:10][C:3]1=2.C(=O)([O-])[O-].[K+].[K+].[C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)(=[O:25])[CH3:24].O>CN(C)C=O>[C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][N:14]1[CH2:15][CH2:16][N:11]([C:7]2[C:4]3[CH:5]=[CH:6][S:2][C:3]=3[CH:10]=[CH:9][CH:8]=2)[CH2:12][CH2:13]1)(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

1.0 g (3.9 mmol) of 1-benzo[b]thiophen-4-yl-piperazine hydrochloride was suspended in 20 ml of dimethylformamide (DMF), and potassium carbonate (1.3 g, 9.4 mmol) and 4-bromobutyl acetate (0.7 ml, 4.8 mmol) were added thereto. The reaction mixture was stirred at 80° C. for 6 hours, cooled to room temperature, and water was added thereto, and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1), and concentrated to dryness under reduced pressure to obtain 4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butyl acetate (0.72 g) as light yellow oil.

Workup

temperaturecooled to room temperature
extractionextracted with ethyl acetate
washThe organic phase was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1)
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-d0b9ca50fbfc4892821483abf8a60284
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071600B2

Reaction notes

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