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

HRID 744692Notes

Reaction equation

HRID 744692 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-8a51cfcb7d234a128c347a2a1a6dcf49
Source dataset
uspto-grants-1996_09
Patent number
US05559143

Reaction notes

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