Ethanol → 6-[[2-(5-Hydroxy-1H-indol-3-yl)ethyl]amino]-N-(3,4-dimethoxyphenyl)-heptanamide, monohydrochloride hydrate

HRID 273814

Reaktionsgleichung

Reaktionsgleichung von HRID 273814
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.[ClH:14].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:25][C:26](=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][C:31](=O)[CH3:32])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].C(O)C>C(OCC)(=O)C>[OH2:7].[ClH:14].[OH:7][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:1]=1)[NH:10][CH:9]=[C:8]2[CH2:11][CH2:12][NH:13][CH:31]([CH3:32])[CH2:30][CH2:29][CH2:28][CH2:27][C:26]([NH:25][C:19]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([O:16][CH3:15])[CH:18]=1)=[O:34]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 160436Serotonin HydrochlorideHCID 15388978N-(3,4-dimethoxyphenyl)-6-oxo-heptanamide

Produkt 1

HCID 1317177896-[[2-(5-Hydroxy-1H-indol-3-yl)ethyl]amino]-N-(3,4-dimethoxyphenyl)-heptanamide, monohydrochloride hydrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound was prepared as in Example 2B except using 178 mg of serotonin hydrochloride and using N-(3,4-dimethoxyphenyl)-6-oxo-heptanamide (225 mg), running the reaction 21 hours at ca. 25° C. The compound as the free amine had an Rf of 0.5 in 10:90 ethanol:ethyl acetate. The title compound was obtained as a tan solid (247 mg). Anal. Calc. for C25H33N3O4.HCl.0.3 H2O: C, 63.37; H, 7.24; N, 8.73. Found: C, 62.58; H, 7.41. IR(KBr): 3348, 1610, 1514, 1450, 1224, 1020, 792 cm-1. CIMS (CH4):440 (100%), 293 (37%) 1H NMR (d6 -DMSO): 10.67 (1H, d; J=2.2 Hz), 9.84 (1H, s), 8.75 (1H, bs), 8.70 (1H, s) 7.33 (1H, d; J=2.3 Hz), 7.17- 7.09 (3H, m), 6.87-6.84 (2H, m), 6.63 (1H, dd; J=2.2 Hz, 8.5 Hz), 3.70 (6H, s), 3.22 (1H, bm), 3.22 (2H, bm), 2.98 2H, bm), 2.31 (2H, bt; J=7.4 Hz), 1.85-1.70 (1H, bm), 1.63-1.32 (4H, bm), 1.23 (2H, d; J=6.4 Hz) ppm. 13C NMR (d6 -DMSO): 172.41, 150.64, 149.10, 145.62, 132.90, 131.52, 128.10, 124.49, 112.88, 112.62, 112.32, 109.01, 105.25, 102.77, 56.43, 56.13, 54.04, 44.88, 36.66, 32.68, 25.53, 24.96, 22.63, 16.26 ppm. Melting Point: 214°-215° C.

Aufarbeitung

  1. customThe compound was prepared as in Example 2B
  2. customthe reaction 21 hours at ca. 25° C

Quellen und Nachweise

ORD-Eintrag
ord-d1383c3022e848a2a4c5b92596dc8aba
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387604

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