Hordenine → Methyl-phenyl-carbamic Acid 4-[4-(2-dimethylamino-ethyl)-phenoxymethyl]-phenyl Ester

HRID 1180050

Reaktionsgleichung

Reaktionsgleichung von HRID 1180050
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10](=[O:19])[N:11]([CH3:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[CH3:20][N:21]([CH3:31])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1>>[CH3:31][N:21]([CH3:20])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([O:9][C:10](=[O:19])[N:11]([CH3:18])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:8]=2)=[CH:26][CH:25]=1

Komponenten

3

Edukt 2

HCID 68313HordenineHCID 69518671Methyl-phenyl-carbamic Acid 4-hydroxymethyl-phenyl Ester

Produkt 1

HCID 69519390Methyl-phenyl-carbamic Acid 4-[4-(2-dimethylamino-ethyl)-phenoxymethyl]-phenyl EsterAusbeute 52 %

Versuchsvorschrift

The title compound was prepared in 52% yield as colorless crystals using methyl-phenyl-carbamic acid 4-hydroxymethyl-phenyl ester and 4-(2-dimethylaminoethyl)-phenol. 1H NMR (400 MHz; CDCl3): δ 2.85 (s, 6H), 2.98-3.02 (m, 2H), 3.17-3.21 (m, 2H), 3.42 (br s, 3H), 5.02 (s, 2H), 6.90 (d, 2H), 7.12 (d, 2H), 7.25-7.43 (m, 7H); HPLC-MS: m/z=405.2 (M+1); Rt=2.91 min.

Quellen und Nachweise

ORD-Eintrag
ord-555f2ca247e945efa89e84d961545d5d
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279470B2

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