Potassium Carbonate → Dimethyl-{4-[4-(3-thiomorpholin-4-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}amine

HRID 272818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272818
[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]1[CH2:27][CH2:26][S:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl.CO.N>CN(C=O)C>[CH3:3][N:2]([CH3:1])[CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][S:25][CH2:24][CH2:23]3)=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 21584172Ammonia methanol dichloromethaneHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 230916864-(3-Chloro-propyl)-thiomorpholine

Produkt 1

HCID 59837475Dimethyl-{4-[4-(3-thiomorpholin-4-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}amineAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1000 mg, 4.25 mmol), 4-(3-chloro-propyl)-thiomorpholine (764 mg, 2,13 mmol), DMF (20 ml), and K2CO3 (2.34 g, 17 mmol) were reacted together according to general procedure B. The isolated material was subjected to chromatography on silica, eluant DCM:MeOH:NH3 (95:5:1) to give the title compound (320 mg, 20%). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 2H), 6.86 (d, 2H), 3.99 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.79-2.64 (m, 8H), 2.55 (t, 2H), 2.40 (s, 2H), 2.16-2.04 (m, 2H), 2.01-1.82 (m, 4H), 1.97 (s, 6H).

Quellen und Nachweise

ORD-Eintrag
ord-8f21ef72450b4ee99703e4fdaebde445
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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