Diisopropylethylamine → 4-Iodo-3-methoxy-N-(1-methylpiperidin-yl)benzamide

HRID 81964

Reaktionsgleichung

Reaktionsgleichung von HRID 81964
[I:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([O:8]OC(C)(C)C)=O)=[CH:4][C:3]=1[O:16][CH3:17].C([N:20](C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:49][N:50]1[CH2:55][CH2:54][CH:53](N)[CH2:52][CH2:51]1>CN(C)C=O.O>[I:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:20][CH:51]2[CH2:52][CH2:53][CH2:54][CH2:55][N:50]2[CH3:49])=[O:8])=[CH:4][C:3]=1[O:16][CH3:17]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27375314-Amino-1-methylpiperidineHCID 86653099tert-Butyloxy 4-Iodo-3-methoxybenzoate

Produkt 1

HCID 666880784-Iodo-3-methoxy-N-(1-methylpiperidin-yl)benzamideAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of tert-butyloxy 4-iodo-3-methoxybenzoate (250 mg, 0.90 mmol) in anhydrous dimethylformamide (8 mL) was treated with N-ethyl-N,N-diisopropylamine (0.63 mL, 3.6 mmol) and TBTU (404 mg, 1.26 mmol). The mixture was then treated with 1-methylpiperidin-4-amine (0.160 mL, 1.26 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction was diluted with water and the resulting precipitate was collected by filtration to afford the title compound (250 mg, 71% yield).

Aufarbeitung

  1. filtrationthe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0c9e7cf7d3ff4f94af6359c374cf9327
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846701B2

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