Potassium Carbonate → {3-[4-(4-Dimethylaminomethyltetrahydropyran-4-yl)phenoxy]-propyl}diethyl-amine

HRID 272834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272834
[CH3:1][N:2]([CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[CH3:3].Cl[CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:3][N:2]([CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[CH3:1]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 669183-Chloropropyl(diethyl)amineHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

Produkt 1

HCID 59837528{3-[4-(4-Dimethylaminomethyltetrahydropyran-4-yl)phenoxy]-propyl}diethyl-amineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (500 mg, 2.13 mmol), (3-chloro-propyl)-diethyl-amine (319 mg, 2,13 mmol), DMF (10 ml) and K2CO3 (1.18 g, 8.52 mmol) were reacted together according to general procedure B. Purification by chromatography on silica, eluant (36% EtOH: 1% NH3 in DCM) gave the title compound as a pale yellow clear oil (160 mg, 22%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.86 (d, 2H), 4.00 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.61 (t, 2H), 2.54 (q, 4H), 2.40 (s, 2H), 2.15-1.82 (m, 6H), 1.97 (s, 6H), 1.02 (t, 6H).

Aufarbeitung

  1. customPurification by chromatography on silica, eluant (36% EtOH: 1% NH3 in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-18d849241ac943bda0f5cf48b5b5646f
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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