Dimethylamine → 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide

HRID 535653

Reaktionsgleichung

C([O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)=O)C.C[Al](C)C.C[Al](C)C.C1N2CC[N:38]([CH2:39]C2)[CH2:37]1.CNC>O1CCCC1.[Cl-].[Na+].O>[CH2:21]([N:18]1[CH2:17][CH2:16][N:15]([C:14]2[C:8]3[O:7][C:6]([C:4]([N:38]([CH3:39])[CH3:37])=[O:3])=[CH:10][C:9]=3[CH:11]=[CH:12][CH:13]=2)[CH2:20][CH2:19]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

7-(4-Benzyl-piperazin-1-yl)-benzofuran-2-carboxylic acid ethyl ester (1.0 g, 2.74 mmol) and DABAL-Me3 (0.56 g, 2.20 mmol) were mixed in tetrahydrofuran (5 mL). Dimethylamine (2M in THF) (2.2 mL, 4.39 mmol) was added and the mixture was heated by microwave irradiation to 120° C. for 15 min. Brine was added and the mixture was extracted with dichloromethane, dried over Na2SO4, filtered and the solvent removed by rotary evaporation. The product was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-2%) giving 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide (0.70 g, 1.93 mmol) in 70% yield.

Aufarbeitung

extractionthe mixture was extracted with dichloromethane
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent removed by rotary evaporation
customThe product was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-2%)

Quellen und Nachweise

ORD-Eintrag: ord-fad5ab25af9f4a149521755b80ec1b68
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08859534B2

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