1-Amino-3-(diethylamino)propan-2-ol → 5-Methyl-2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-methoxy-1-phenylindole
Reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]=1[C:19](O)=[O:20].[NH2:22][CH2:23][CH:24]([OH:31])[CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28]>>[CH3:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]([C:19]([NH:22][CH2:23][CH:24]([OH:31])[CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:20])=[C:3]2[O:2][CH3:1]Participants
3
Procedure
The above 3-methoxy-5-methyl-1-phenylindole-2-carboxylic acid is converted into its acid chloride analogously to Example 1H, and this is reacted with 1-amino-3-diethylamino-2-hydroxypropane. The title compound is obtained as an oily base. This base is dissolved in isopropanol, and citric acid is added to the solution. The citrate of the title compound which has precipitated is filtered off with suction and recrystallised from isopropanol. Melting point: 126°-128° C., yield: 7.7 g.
Sources & evidence
- ORD record
- ord-d7227f7534084786a1ca6957a690239b
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04924004
Reaction notes
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