Methyl iodide → 4-(2-Ethoxy-2-oxoethyl)-1,1-dimethyl-4-(3-(4-octylphenyl)ureido)piperidinium iodide

HRID 1192887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192887
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=2)=[O:10])[CH2:4][CH2:3]1.[CH3:32][I:33]>C(Cl)Cl>[I-:33].[CH2:30]([O:29][C:27](=[O:28])[CH2:26][C:5]1([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=2)=[O:10])[CH2:6][CH2:7][N+:2]([CH3:32])([CH3:1])[CH2:3][CH2:4]1)[CH3:31]

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 66865126Ethyl 2-(1-methyl-4-(3-(4-octylphenyl)ureido)piperidin-4-yl)acetate

Produkt 1

HCID 668652964-(2-Ethoxy-2-oxoethyl)-1,1-dimethyl-4-(3-(4-octylphenyl)ureido)piperidinium iodideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-(1-methyl-4-(3-(4-octylphenyl)ureido)piperidin-4-yl)acetate (73 mg, 0.169 mmol) in CH2Cl2 (5 mL) was treated with MeI (0.11 mL, 1.69 mmol) and the reaction stirred overnight at room temperature. The solvent was removed in vacuo to yield crude title compound (95 mg, 98%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.35 (bs, 1H), 7.42 (d, 2H, J=8.4 Hz), 7.05 (d, 2H, J=8.4 Hz), 6.49 (bs, 1H), 4.39-4.32 (m, 2H), 4.14 (q, 2H, J=7.2 Hz), 3.41-3.34 (m, 5H), 3.21 (s, 2H), 3.20 (s, 3H), 2.64-2.41 (m, 6H), 1.29-1.20 (m, 13H), 0.89 (t, 3H, 6.4 Hz); MS ESI 446.4 [M]+, calcd for [C26H44N3O3]+ 446.65.

Aufarbeitung

  1. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4994e647745f44b6a610b78afda9e35f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680282B2

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